You're Wrong About
You're Wrong About
Where Have All the Preppies Gone? with Avery Trufelman
Put on your Docksiders for a stroll through history with Avery Trufelman, who shows us how Ivy style became “preppy,” and how preppy fashion escaped the campus and took over the world. We’re talking about clothing, class, race, and the American dream: you may be through with the polo shirt, but the polo shirt isn’t through with you.
Here's where to find Avery:
Articles of Interest on Substack
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Sarah's other show, You Are Good
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https://articlesofinterest.substack.com/
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https://www.podpage.com/you-are-good
http://maintenancephase.com
Sarah: Tucker Carlson looks like an evil, little boy in a horror movie from the seventies, doesn't he?
Welcome to You’re Wrong About. I'm Sarah Marshall, and today we have Avery Trufelman as our special guest. Today we ask the question, where have all the preppies gone? An extremely topical reference to a Paula Cole song, which I'm sure is on all of your minds. And we are talking today about how an aesthetic that once was, or at least seemed to be a hyper-specific marker of class, race, and privilege, has now become something we hardly even notice and may seem like it's disappeared. But in fact, escapes discourse simply because it has become ubiquitous.
I loved having Avery on the show. I've enjoyed her work in podcasting since before I made podcasts, and she's one of my inspirations for getting into doing this at all. And it was so wonderful to talk with her about something that she has clearly become deeply obsessed with. And there's nothing I love more than being told about somebody's obsession with footnotes.
If you want to support the show, you can do it on Patreon or Apple+ subscriptions. And we are coming out with a bonus episode where I talk to Carolyn, our wonderful producer, about the making of Fleetwood Mac’s Rumors. And we've got some cute shirts and stuff on Tee Public as well. I've heard that people are shopping lately. I don't know why, but if you want to, that's one of your options. Thank you so much for being with us. Here's our episode.
Welcome to You Wrong About, the podcast where I have a little cold. It's not Covid. I'm going to be here forever, don't worry about it. And with me today is Avery Trufelman, podcasting legend, dare I say it.
Avery: It's such an honor. This is so cool.
Sarah: This is so fun to have you on here. Tell us about who you are and what you do, and then we'll go on our wonderful cable knit journey together.
Avery: Yeah, I'm a podcaster. For the last year or so, I've been working on this podcast that I make about fashion called, Articles of Interest. In the past, episodes have each been about one thing, like what's the history of plaid or what's the history of knockoffs? Just like one, that's why it's called Articles of Interest. Each one's an article of clothing. And I was going to do one episode about the topic we're going to talk about today, and then I was like, wait, no, this requires its own thing. So I've made like a seven-episode series about preppy clothes, and I'm convinced it's the great American fashion story.
Sarah: I'm excited. I wanted to start by telling you my perceptions of preppy-ness, preppy clothes. Because when I first heard from you about doing this idea I was like, I mean I really like it. I would love to do it, but is there enough material there? And then we had a conversation about it ,and I was like, oh my God. It's about everything.
Avery: I have to say, at cocktail parties and people are like, “What are you working on?” I’m like, “Hear me out. It's about preppy clothes and I think they're a style of clothes.” Well, first of all, they look boring. They look like there's nothing to them. And also, everyone has so much baggage around it whether you're like, I hate it, or I'm embarrassed that I used to wear it, or I don't know. People are like, ugh. It's a deterrent. What are your associations?
Sarah: I'm going to start in a place I bet you were expecting, Ted Bundy. And the thing about Ted Bundy I've always thought, is not that he was great looking, because just look at him. Yeah. But that he was incredibly white and that he was both born very white and then was inhabiting and enacting this much greater degree of whiteness in order to make victims trust in him. Because famously he would walk around wearing tennis whites and it's like, you've been playing tennis, Ted?
Avery: That's the insidious power of these clothes. You know the members of the, back then, alt-right marching in Charlottesville. They're all wearing polo shirts with their tiki torches, and they were trying to look approachable. They were trying to be like, come on, join us. “We're not that scary”, they say, marching with tiki torches.
Sarah: Come on down to the BMW dealership and talk about white supremacy and how Jews will not replace us. Come on down. We're nice. We just are white supremacist and fine with the Holocaust.
Avery: 100%. And that's why Tucker Carlson is wearing the most impeccable, preppy uniform.
Sarah: Tucker Carlson looks like an evil little boy in a horror movie from the seventies, doesn't he? It didn't occur to me before, but he really does.
Avery: But that, and that's the thing, it's always like masking the same thing. They're saying these wild bombastic things with this uniform, or in Ted Bundy's case, doing these awful things with this uniform of presentability, looking like a rational, normal, friendly white neighbor.
Sarah: I would also submit that guy in St. Louis who came out onto his porch of his mansion with, I'm going to get it wrong. I always get guns wrong with a giant gun. Because protestors were going by his yard.
Avery: Wearing a Brooks Brothers polo. Yes.
Sarah: Yes. So we have Ted Bundy, Charlottesville Nazis, say hello to my little husband. And to that, I'm going to add James Spader in Pretty in Pink . The Preppy Handbook, which is a book whose history we will get into if you haven't heard.
And yeah, I think that establishes us pretty well. And to speak of actual clothing, what I think of are cable knits, pearl earrings, intentionally slightly unraveled hems, and edges of things. LL Bean of course. Especially the Bean Boot. I would argue puffy vests, down vests even are in there, if you're in like Maine or something.
Avery: Totally. Patagonia, the cannon of what preppy is, is constantly expanding, too. I would say Patagonia vests are preppy, but that's like a recent addition to the canon, right?
Sarah: So it's not like old school preppy, but it's new school preppy. And also that it's an aesthetic. And this is maybe the thing I find most intriguing that people had such a clear grasp of for a period and was such a socially dominant idea and that now we don't talk about, now there's all these other words for areas of fashion or kind of mood that intersect with preppiness.
I think dark academia is one and I don't know any of the others. But it's like a term that has vanished from the zeitgeist and yet as you're already pointing out clearly, the thing itself has gone nowhere.
Avery: So that's the interesting thing in the series, I was talking with the writer Ta Lavin. We were talking about Charlottesville and the preppy look that was used in Charlottesville. And he was saying that group of people was then called the Alt-right, and that is not a word you hear anymore because that is what the right has become. It was so successful that you don't need the word anymore.
And I would argue that is what's happened with preppy itself because it is so ubiquitous that we don't need the word. And if anything, those kinds of clothes are just considered basics or classics. If you go into any Uniqlo and you really look at it, really look at what they have on the mannequins, it's preppy. In the eighties someone would've been like, that's a preppy look. And now it's just like a baseline thing.
Sarah: And I guess to speak of the polo shirt, it's the shirt of, “say hello to my little husband”. It's the shirt of camp counselors and pool snack bar staff. And to me, most significantly, it's the shirt that my mom wore practically every day of my childhood. Because she was a doctor in a sort of business casual setting, and she didn't feel like dressing particularly feminine. And I think that a polo shirt was as close as anyone can get to wearing nothing of any description at all. I have no idea where this could begin. I feel like you could say like 1940 or 1552.
Avery: Really, I think where the story begins is in 1818 in the United States, with the birth of a store that would eventually become known as Brooks Brothers. And it all starts with a merchant named Henry Brooks in downtown New York. And this is the funny thing. I really thought while researching preppy clothes, I'd be going out to Kennebunkport to interview people named Biffy all the time. But really, it's a very New York story. It is a super New York story. Basically Henry Brooks runs a grocery store in downtown New York on Catherine Street. He works by the docks. So the British and the US were enemies in the war of 1812. They were still getting over that whole American Revolution thing. Tensions were high, and what they functionally do is like a prank.
Before America started enslaving people in the south to grow our cotton, we bought all our fabrics from England. And obviously in the war of 1812, we weren't buying any fabrics from England because they were the enemy. And basically after the war ended, England was functionally like, all right, let's mess with them. Let's just dump all of our unused fabric in the port and it backfires.
Sarah: Wow, that's great.
Avery: I don't know what they would've expected to happen from this, but people like Henry Brooks see all this fabric pile up in the port and they're like, oh, this is interesting. I mean, it's important to note at this time you don't go shopping for clothes. That's not something that happens unless you're poor.
What people aspire to go shopping for around this time is cloth. You go shopping for cloth and then you sew it up yourself or you take it to a tailor, clothes are made for your body and if you are buying already made clothes, you're buying them secondhand from a rag distributor. It's not anything cool, it's not anything to be proud of. They probably are really ill-fitting, that's for the poorest people in society.
Sarah: I love how I think of ourselves as living in this time of great privileged fashion-wise and having all these choices and I bet like people from the 1850s would be scandalized and embarrassed for us. Look, I'm just wearing this rag from an H&M on the freeway. That's just like some cloth.
Avery: Ugh. I have been told that the hallmark of modern fashion is that nothing actually fits. We have two modes of fit, which is oversized or stretchy, and that's the only way that clothes actually fit us now.
Sarah: Yeah. Which is also nice to remember when you feel like none of your clothes fit. Yeah, because they don't.
Avery: Yeah, they don't. They're not supposed to. Yeah. So Henry Brooks sees all this fabric pile up. And this is a moment very notoriously in New York where the population of the city - this is the early 1800s - New York's really getting going. The population is doubling all the time. All the time. There's so much access to labor. He and a bunch of other merchants take advantage of all this cloth that is piled up in the ports of New York. And they're like, what if we got people to just draw patterns and then women can sew this stuff up at home. And this is different from a tailor used to be a venerated artisan. And this, we'll just give it to these women, and they'll sew it up with their children or whatever. And then you can have new, decent quality, ready to wear clothes.
Sarah: Is this the moment at which the sweat shop was invented?
Avery: I mean, I can't, I don't know that definitively, but it is this kind of landmark moment in the mass production and the commodification of labor. Also it’s this deeply American thing. And so at first, this is really for people who work by the docks. People who never thought they'd have a suit and now they can buy one ready-made.
At this point, the word democracy is a dirty word. It's almost like how socialism is now. People are like, could this even work? It's not like it was a dirty word in the States, it was more like it was a dirty word in Europe. People are like, oh my god, our petulant colonial children want to go off and start this democracy, this full democratic government. Let's see if they can pull this off. European diplomats were always coming to the U.S. to be like, let's see how this experiment is doing. And by the 1840s, it was this very famous cliche that they would always write back like, “Oh my god. Everybody in America dresses so well.” It was this huge advertisement for what democracy was capable of doing.
And actually, I mean, an interesting thing is that in New York, it provided a lot of class anxiety. Because the poor people weren't in rags. The rich people weren't in jewels and wigs. Everyone’s in these ready-made suits. So everyone is wearing this uniform. Benjamin Franklin called it our “happy mediocrity”. It's a democracy. We're not copying the fashions of a monarch, we're all trying to look like each other. There are no ready-made clothes for women. That didn't happen until the late 18th century.
Brooks Brother, again, it was one of many clothing companies that started making mass produced clothes in America, but it's the only one that's still around. It's over 200 years old. It has clothed 40 out of 46 presidents. But the reason they did it was such a powerful statement that, oh my god, the most powerful man in the nation dresses the same as the small-town merchants and the conmen.
And these mass-produced clothes were able to be shipped all over the United States so you could get people in like small towns also wearing Brooks Brothers suits. So it was this incredible emblem of everything that is wrong and fascinating and interesting about democracy and our idea of democratic dress.
Sarah: Yeah. And is it fair to say that Brooks Brothers started off as Forever21 for Stevedores?
Avery: I would say so. I love that.
Sarah: They should be proud.
Avery: Stores like Brooks Brothers and their contemporaries created the modern shopping experience. Especially once Brooks Brothers started making high-end, mass-produced clothes in 1850, this is the first time you'd go to a store for entertainment and walk out with something. You used to be like, oh, I guess I got to get some clothes. And you touch a bunch of fabrics, and you get measured, and you're like, I guess I'll pick these up later. But it was the first time that you could go in and be like, who do I want to be? And you could try on different clothes and walk out of the store with something. Shopping as an activity happens around this time. And that's America.
Sarah: Right? And they're listening to John Phillip Souza music or something.
Avery: That crazy, new-fangled Souza. A lot of people are like, “Oh, preppy clothes began in the UK.” But I think it really begins as this very American thing with the start of Brooks Brothers.
Sarah: Which I think is just fascinating because it shows, if you buy that argument, which I do, that Preppiness has always been about American class mobility, that there's no original that anyone's trying to copy. We're all just doing copies.
Avery: Yes. We're all supposed to look towards each other. So I couldn't nail an exact date on this, but Brooks Brothers eventually makes the turn to making what we would now call ‘preppy clothes’. But back then the style was called ‘Ivy’. It was like the ‘Ivy look’. And that really came from Princeton University. That really came from the fact that Princeton is this tiny, homogenous, and it has these things called Eden Clubs, where it's not regulated by the university. So it was these privileged, young, Anglican men hanging out together and developing this new style separate from everything else and separate from their parents. And most of what that style entailed was a version of what you see college students doing today. Which is wearing their sports clothes all the time.
Sarah: Right. Athleisure, invented by Khaled and Hockley.
Avery: It's arguably a precursor to Athleisure. The Oxford button down shirt started as something that polo players in England would wear to keep their collars from flopping up while they rode horses. And a lot of these clothes were adapted and manufactured by Brooks Brothers.
Students in Princeton were wearing this sort of new sporty look. Magazines were writing about it. It was known as this thing like, oh, the style on the campus of Princeton was very popular in the 1930s. And that's very like tweed pants and this collegiate young man look. The look starts to expand when admission to college starts to expand, which is obviously like the GI bill.
Sarah: We must know who's really in college.
Avery: Yeah. This is when khakis get introduced. Because khakis are military surplus clothes. This is when veterans are coming to college campuses and they're wearing elements of their military issued uniforms. And the preppy kids are like, oh. The kids who actually went to preparatory high school are like, oh, those are cool pants.
Students at women's colleges were dressing in this way that was arguably sort of androgynous, but that was okay when you were in school. And then obviously when you graduated, you had to become a secretary and get back into dresses.
And then at Morehouse and Spellman, people were wearing Ivy clothes, too. It was becoming this look of Black students, women students, the middle class, it started really spreading. And the fascinating thing is, the old boys at Princeton still kept it. Which goes against everything we think about trend proliferation. If everybody has it, it's no longer distinctive and it's no longer cool.
And then the fascinating thing is there are all these Jewish tailors that make this super waspy, preppy, elitist look. And they've been doing this for a long time. They started doing it in 1902. Since the early 1900s. I talked to this very preppy brand called J. Press and they were like, oh yeah, all the tailors, Jewish tailors figured out how to really make this look something that could extend beyond Brooks Brothers to everyone. So 1940s to 1950s, the look is sort of everywhere.
Sarah: And why do you think that is? Like, personally?
Avery: I talked to this author Jason Jules, who wrote this great book called Black Ivy Revolt in Style. And what he talked about was the role specifically that black activists and jazz musicians had in helping the look spread. Because if you look at Miles Davis, he's wearing preppy clothes, he's wearing an Oxford button down collared shirt. John Coltrane, these musicians look impossibly cool.
And so there was this version of Black Ivy that was just a variation on what the Princeton students were doing. And these Black jazz musicians would tour notoriously around Europe and spread this look around and became the accidental ambassadors. Like, hey, look how awesome, how relevant this American look continues to be. As it expanded, the style only got more interesting. Middle-class veterans brought in the khakis and women brought in this element of androgyny.
Every time people took on this look, they only made it more interesting. So while I'm sure there was some grumbling at the Eden club of ,they’re stealing our stuff, I want to believe that there was actually some interest and intrigue and delight in the way that this is happening. Which is fascinating as a fashion trend.
Sarah: And this actually is an example of something succeeding in the marketplace of ideas. And yeah, it feels like it's both pretty basic and I just mean like literally basic and also very capacious, right? It's like very simple rules, but then it's like a grilled cheese sandwich. You can make 1000 kinds of grilled cheese sandwiches because it'll all be a grilled cheese sandwich.
Avery: Yes. Yes. Obviously, the look goes away in the sixties. So you can see this most notably at the 1968 Olympics in Mexico City when Tommy Smith and John Carlos very famously raised the Black Power fist on the podium. You're seeing fashions change in real time. Because in some photos of them they're wearing this sort of Ivy look, they're wearing a button-down shirt. And then at other moments they're wearing leather jackets and beads and it's like, change is in the air.
A lot of historians chalk this up to the deaths of Martin Luther King and JFK and RFK, and this sort of disillusionment with the happy mediocrity that Benjamin Franklin once advocated for. This idea that to do our best in this society in America, we all have to work really hard to fit in. That's suddenly not working anymore. Suddenly there's this new era of rebellion.
And one of the things that happened in the fifties was this revolution in management theory. Where this MIT professor realized that the way people were told to go to work was a system of sticks and carrots, basically. You should go to work and you're going to be heavily observed and rated, assessed for maximum productivity. And he was like, this is clearly making people miserable.
Sarah: Jack Lemmon in the apartment.
Avery: Yeah. Exactly. Exactly. Yeah. They're all these movies about all the fifties Malays. And so he called that Theory X of Management. And he was like, what if there was a new form of management? And he called it Theory Y. This was known as the creative revolution where it's like, what if we encouraged people and encouraged workers to work because they feel fulfilled? Less supervision. This is setting the seeds for Mad Men, the creativity of your work should fulfill you.
What this means is that as much as we like to think that the establishment, the men in the gray flannel suits, were upset by the counterculture in the sixties. The creative, hip, young ad executives were all in on the creative revolution. They love this idea. They were like, rock on. They saw the counterculture and they were like, this is great. Let's lean into this.
And this is when you get all these advertisements, like the 1960s Pepsi campaign that was like, it's for the Pepsi generation. Like everything sold was very groovy and young and cool in this very mainstream way. There's this huge revolution that youth equals cool in the 1960s.
If you look at pictures of college students in the 1950s, they just look older. Because looking older and more mature was the way you were taken seriously. And in the sixties it flips and people are like, I want to look young. So there's this huge advertising revolution. And then part of that is this fashion revolution called the Peacock Revolution. And this is part of why you see people in the sixties and seventies wearing outlandish clothes, just dressing ridiculously. Especially men, they're wearing high heels and they're wearing Nehru collars and frilly collars and Pucci patterns.
Sarah: I think of men wearing like Jeremiah Johnson outfits. Just leather and fringe and full Western Daniel Boone kind of thing.
Avery: Totally. And this is like the beginning of retro fashion. Basically the fashion industry is like, okay, let's just crank out as many looks as we possibly can. Which is really hard to do. And so what they do is they go back in time. The easiest thing you can do is borrow from the past. So if you look at the sixties, it's just like all eras get revived all simultaneously. It's Victorian era, Edwardian era, Western fashion, bam, bam, bam. It's just all happening all at once.
Sarah: It's so funny to think of that happening then, because I feel like that's what fashion is today in many ways. And we're doing Y2K stuff and everything. But thinking about being revivalist about fashion at a time when you're like, I don't know, let's do the Victorian era. It's like, what?
Avery: No. If you look at Yellow Submarine, it's like Edwardian.
Sarah: Yeah. And now that you say that, I'm like, yep. That's what John Lennon looked like for a while there. All these hippies who want to dress like Bob Cratchit.
Avery: Yeah. So basically it becomes this confusing flurry, and it comes on so hard and so fast that it makes trends themselves seem like one giant trend. Oh my God, all this fashion is happening now. And so the easiest return is back to preppy clothes.
Sarah: There we go. They’re back.
Avery: But this time it comes with a twist because most notably in the 1960s, it is revived by a man named Ralph Lauren.
Sarah: Hi, Ralph Lauren.
Avery: And so Ralph Lauren is this Jewish guy from the Bronx, who dropped out of community college or city college who went to Brooks Brothers. Well, he was first and foremost very inspired by the movies. He was very inspired by Fred Astaire and these Hollywood style icons. And because of that, when he was about 20 years old, he works for a year at Brooks Brothers. And that's where he learns about this casual, elegant, Ivy style. And functionally, young Ralph Lauren - he was born Ralph Lifshitz, but he changed his name in high school - he's been Ralph Lauren for his whole life.
Sarah: I like the idea of doing that. Like before you can do it legally, you're like 16 years old and you're like, I'm Ralph Lauren!
Avery: I'm Ralph Lauren. And some people speculate it’s because of the movies, Lauren Bacall or something. I think there's something very dreamy about it. Like this little kid loves film.
Sarah: Totally. First name, boy name. Last name, girl name.
Avery: In the 1960s when everything is in fashion all at the same time and it's this confusing, retro blur, preppy is like this breath of fresh air. People are so amped on it. And so when Ralph Lauren comes out with these preppy clothes, basically what he does is he mixes Hollywood style and Brooks Brothers style. He is like, what if we took these preppy clothes and made them tighter and sexier? And people love it. People eat it up. They're like, I'm so sick of all these fashions, all these wild, retro fashions. I like the simple style. And you can slowly see it ramping up all throughout the seventies.
In 1974, Ralph Lauren did the costumes for the movie, the Great Gatsby. And then you have this rash of movies that take place just before Kennedy was assassinated. You have Animal House and American Graffiti.
Sarah: Laverne and Shirley. Yeah.
Avery: And so everything that you're saying, this idea of oh, wasn't it cool to be just like a simple, young teenager before the world got so complicated? It's the premise of almost every movie. Or not every, but all these huge movies in the seventies.
Sarah: And of so much fashion. Like it's so funny to me that Y2K fashion is in because I don't know, it's just funny. It made sense to me when we were doing fashion waves based on stuff I wasn't already an adolescent for. But now I'm like, oh. But it makes total sense. You're just like, remember when you just had your Delia’s catalog, and your biggest worry was Y2K.
Avery: I've been thinking about this a lot because I was just watching this talk that Arundhati Roy gave in 2003, and it really reminded me what an awful time that was. Fashion is literal nostalgia when all you look at are like the crop tops and the flip phones. You're like, fun. But then I was like, oh, right, we didn't know why we were in Iraq. The government was lying to us and there was all this enforced nationalism. And it was just like, really scary. That was a really awful time.
Sarah: Yeah. Maybe the truth that's hiding behind that is that times are often equally awful in their own way because people are awful in consistent ways. There's a consistent thread or in terms of what America is. Yeah. The time around the Iraq war, the beginning of it and the weapons of mass destruction allegedly was this time of great. Either you are actively avoiding the truth that is as clear as the nose on your face or you're not a patriot and you're actually like a traitor. And also there was a great mainstream embrace of that too.
Avery: For all of the grief that we give the Twitter discourse now, at least there is a discourse.
Sarah: For a little while, yeah. Our discourse was Alan Jackson songs.
Avery: So Ralph Lauren. I had never thought about Ralph Lauren before. Ralph Lauren is just so ubiquitous. I looked in my closet. I was like, oh, I guess I have Ralph Lauren's stuff. I don't even remember buying it. It was never anything I sought out. It was just there.
Sarah: It just wanders in. I know him, of course, as Rachel Green's boss.
Avery: Oh, right. And he was in that, right?
Sarah: Yeah. At least once they had a Ralph Lauren cameo. But that was great. Like the pilgrim's progress of Rachel Green ends at Ralph Lauren because she comes to New York, she wants to work in fashion, and boy is at a gradual crawl to Ralph Lauren. Which is like, yes, our girl has finally made it.
Avery: I think what Ralph Lauren has done is functionally up there with Steve Jobs. I was talking to a contemporary of Ralph's, another menswear designer. And he was saying, at the time we were both coming up, the way that people found out about new designers was through department stores functionally in New York, the way you learned about a new designer was Bloomingdale's. And if you were a designer selling your wares at Bloomingdale's, they would put your shirts in the shirt section and your pants in the pants section and your socks and the socks section.
And Ralph was really the first, I was like, can you put all my clothes together? Because this is all like part of a world. And so they carved out a section of the ground floor. Ralph Lauren has this famous quote that was like, “I don't do shoulders, I do worlds”. And what he means is you don't come to me for the tailoring. It's not about oh, check out, I have these buttons and these shoulders. He was inspired first and foremost by the movies. The whole thing is like, come into my world. Right? And he showed it in these ads that looked like film stills and they were everywhere, these multi page spreads. And you go into his store, and you can see how all the clothes fit together. And even now, if you go to his flagship store, it's like Epcot. He's got the preppy wing, and the safari wing, and the western wing. It's the world of Ralph Lauren. It's what we hear now, it's ubiquitous like lifestyle marketing.
Sarah: God. Yeah. It's FAO Schwarz for adult men.
Avery: Yeah. He is a pioneer of lifestyle marketing. Yeah. And also in these ads, he's like showing you the full context, it's not just about the clothes, but it's about driving in your car with your beautiful blonde children or being on a ski lift with your handsome fiancé. He shows you the full context of where these clothes supposedly belong. And he sold this image, and it was ascendant.
So the seventies into the eighties, there's like this slow boil of all these nostalgic movies and Ralph Lauren is on the ascent. And then the way that I like to say it is like it had a long fuse and then the match was really lit in 1980 by the Preppy Handbook. And the word “preppy” has been around at least since the 1930s, but that wasn't a widespread word because most people didn't know that world of preparatory high schools that look like tiny colleges that is so elite. How would anybody know that's a derogatory term? But it was brought into the mainstream consciousness by this movie in 1970 called, Love Story.
Sarah: What can you say about a 25-year-old girl who died?
Avery: Beautiful.
Sarah: Yes. Love Story.
Avery: Love Story, which apparently popularized the name, ‘Jenny’.
Sarah: What?
Avery: According to this historian I talked to, and if you look on Wikipedia, it was a hugely popular movie and it popularized the name Jenny. And there's this moment where Jenny is like, “Get your own library, preppy.” And is ridiculing her handsome boyfriend, played by Ryan O'Neil. She ridicules him for being a preppy, and that catapults the word into common parlance.
And also it should be said, around 1972 is the moment when Ralph Lauren introduces the polo shirt. And this is when preppy style starts to emerge as something different from collegiate ivy style. So the actual original polo shirt was invented by Jean Rene Lacoste, a tennis player in France in 1927.
Sarah: Oh my God. It's a person. A guy named Lacoste.
Avery: His nickname was ‘the crocodile’. And I forget why. There are a few reasons. Some were like, because he had a big nose. And others were like, it was his playing style. But whatever, Jean Renee Lacoste was called ‘the crocodile’. And you used to play tennis in long sleeve dress shirts. And he was like, what if we didn't? And he invented the short sleeve knit sport shirt, and it was pretty much used for tennis and it was really rare. It was hard to get in the States if you were going to Europe.
I talked to someone who was like, oh yeah, I remember going in the 1960s, people would be like, can you bring back a Lacoste shirt? And then in the seventies, 71, 72, I forget. Ralph Lauren basically makes a version of it. And it's so interesting because Ralph Lauren's company is called Polo. It's named after this sport that you have to be super rich to play because you need multiple horses. And what the polo shirt actually is, is a tennis shirt. It's a shirt for playing tennis, but we call it the polo shirt because that's the name of the company. So it's the wrong sport, but that's what we call it.
Sarah: That never occurred to me. Right. Because who even knows what you wear to play polo? You can't go play polo at the park on a whim.
Avery: Right, right. And so, and now it's just become a brand, it's become like Kleenex, we call the style basically after this brand. So, but this is all tacitly brewing throughout the seventies until in 1980, this woman who was working for the Village Voice goes to this publisher because she has an idea for a joke book. She wants to publish a book of light bulb jokes like, how many X does it take to screw in a light bulb? And they're like, actually we have another idea for you. Do you want to make something called the Preppy Manual? And it almost feels like the discourse around preppy is like how early aughts hipsters were. It's like, ha ha, we all love to laugh at them.
Sarah: Yeah. No one will admit to being one. But we all make fun of them, right? Because the funny thing about hipsters is that I don't really think there have ever been any self-identified hipsters. It's always what some other guy is doing. There's always a mustache bigger than yours.
Avery: Totally. Totally. Although I have to say, I was very proud of being a hipster. I was like, we have a movement of something. No, but it totally, it was totally like a derogatory thing, and I think this writer for the Village Voice went to a prep school. She was another Jewish New Yorker, went to an Ivy League school, understood that she was this thing, that she was a preppy and she thought it was just funny. It was like a joke. She laughed about it. And when Powerhouse Books was like, do you want to write the preppy manual? They gave her 10 weeks to write it and $7,000. And she was really young. She had just graduated, and she was like, I'm going to write the best book I can.
Her name's Lisa Birnbach, and she went on to do an anthropological study of what her friends in prep school and in her Ivy League school, not only what they wore, but really the underlying philosophies of how preppy people think and shop and learn. Her whole thing was, well, this is mostly going to be read by my peers and my contemporaries who go to Loomis Chaffee and all these prep schools. So I have to make it right. I have to be really accurate.
She turned in the book two weeks late, so it was like a 12-week dash she wrote this book. And they really didn't think it was going to be anything. They thought it was like a coffee table book. And their big hit that year was supposed to be this book that they were writing called, How to Make Funny Noises with Your Mouth, or something to that effect. They were not expecting this to be anything. And then it sells 2.3 million copies. It's this runaway…
Sarah: I had no idea it was that successful. That's incredible.
Avery: It was huge. It launched all these other copycats, there was the Jewish American Princess Handbook, the Valley Girl Handbook, all these handbooks. And it also launched all of these books like Paul Fussell's Class ,about what is social class in America, right? This thing that we had been ignoring since the Brooks Brothers Democratic revolution of no, we're all the same.
And if you look at ads in the eighties, all of them are like, you have the privilege to use this credit card. In the eighties, there's suddenly this idea, in the sixties when you were told to buy things to prove how youthful and rebellious and free you are. In the eighties it was like, prove that you are high class. And that you have moral worth.
Sarah: My kind of example of what the eighties, or at least early nineties, felt like an advertising is the Fancy Feast commercials that Lauren Bacall did. Which I think was also important in helping to destigmatize commercial voiceover work for celebrities. So that's exciting. And the voiceover was always, “Good taste is easy to recognize”.
Avery: Oh my god.
Sarah: Because even your cat, I'm being a little bit silly by saying this, but it's true. Even your cat is a class signifier.
Avery: No. It is, no, Sarah, you nail it. The subtext of the Preppy Handbook is that it was this reveal to mainstream America. They were suddenly getting all these glimpses at how the elite, or at least the upper middle class, not the astronomically gazillionaire, what Paul Fussell calls ‘out of sight wealth’, but what the upper middle class, how they live. And it pulled back the curtain on this world of class signifiers that, oh my God, people are noticing what brand of shoes I wear or how I tie my tie, or whether or not I wear a belt or what watch brand I have that this is all saying something and that it all matters.
The funny thing is the Preppy Handbook is ostensibly a joke. It's a joke book. And Class by Paul Fussell is also supposed to be like a joke book. Because America's like, ha ha ha, we don't really have class, but if we did it's this dry look. Because if you actually talk about it seriously, it's quite upsetting. But Paul Fussell has all these things. Like not smoking at all is very upper middle class, but if you call attention to it, that drops one to middle class immediately. And that upper middle-class people name their cats Clytemnestra or Tchaikovsky. That everything you do, even including your cat and your cat food, everything is this marker of class. And we see that in the same year that the Preppy Handbook comes out. We see that manifested also in the election of one of the two presidents who don't wear Brooks Brothers. Which is Ronald Reagan.
Sarah: Whoa. I would not have guessed that. I would've guessed Carter.
Avery: He was the other one, Sarah!
Sarah: He was the other one!
Avery: But as you can imagine, they do it for opposite reasons because Brooks Brothers is supposed to be traditionally the mass-produced cloth of the people. And Carter is almost too modest, even for Brooks Brothers, his whole thing is he doesn't wear Brooks Brothers. He wears flannel shirts, and he wears just an off the rack suit even for his inauguration, for the time you're supposed to be fanciest. He's almost too humble.
Sarah: Very Mr. Smith goes to Washington.
Avery: Totally. And America isn't having it. He's like, well, we should all close gas stations on Sundays. And America's like, no, absolutely not. We don't want this level of humility. And so the next president they elect, he's the closest America gets to aristocracy, which is a celebrity. And he does not wear Brooks Brothers because he is above Brooks Brothers. He's custom suits from Hollywood.
Sarah: Of course. You need a custom suit when you're crushing unions. Off the rack won’t do!
Avery: Exactly. And so it all ties up with this idea, Reagan's whole idea of trickle-down economics. Well, if you're a wealthy person, you're a moral person. You've worked hard and you don't need to be regulated with taxes. You can be counted on to share it by letting it trickle down. And so this idea of class and money gets really equated with moral worth. And how do you prove that you have moral worth, that you're dependable and that you're trustworthy. It's through these class signifiers and all of this just makes preppy stuff take off.
And at the same time, so many people are getting into business school and trying to enter the professional sphere. And this gets back to your mom, women are entering the professions for the first time. There's this really significant thing that happens in the eighties where women start wearing modest professional clothes, in part because they're following the rules set by John T. Malloy and Dressed for Success and his companion book that he wrote for women. He's like, oh, adopt a practical uniform. And so they do that, and preppy clothes fit right into that.
And then there's this really interesting thing that happens in the eighties where the fashion machine keeps chugging. They're like, oh, cool. That preppy androgyny thing that we were trying, that was like a fun thing, but let's do - they call it frou frou, miniskirts and big shoulder pads and corsets. They're like, yeah, and you can see it. They're pushing it on TV, in ads. All the manufacturers like Liz Clayborne paused production on some skirts to have them shortened. Everyone gets on board with this frou frou thing. And the consumer for the first time ever is like, no, absolutely not. I'm not going to do that. They just didn't buy it.
Sarah: They're like Miranda being invited to do anal Lingus, I'm not going to do that. I don't want to do that.
Avery: Exactly. They're like, no. They had jobs, they had lives. They're like, fuck you. I'm not going to wear a miniskirt. I'm a professional now.
Sarah: Well, and I feel like in that kind of design and culture, there's this tacit concept of don't dress sexy, or the boss will grab you. And in reality, your boss will grab you no matter how you look if they're the grabbing kind, I would submit. And we should all be able to dress as sexy or not as we wish to. But I feel like that's part of the unspoken contract of that fashion as wealth.
Avery: Well, really it's this moment where the consumer is no, you give me what I want. The designer's not going to dictate to me anymore. I want to choose to follow fashion as much or as little as I want. And this is when brands start flipping out. And this is when the trend forecasting industry really grows in the eighties. Because brands are like, oh my God, how do we give the consumers what they want?
And then from that point on in the eighties, the French philosopher [inaudible] says that modern fashion has these three phases. One is up until the 1960s when it becomes about being youthful. And then the next changes in the eighties when the consumer sort of decides what they want. And it means there are multiple competing trends all at once, starting in the eighties. And it also means that the easiest, safest bet for clothing manufacturers, for mainstream clothing manufacturers, is just to make boring stuff. Just make simple conservative clothes and some version of preppy fit right into that, so much so that 1983 is the year that a company called Popular Merchandise Inc. rebrands and becomes J. Crew. It just becomes like a very safe bedrock for any company to pin themselves to is oh, this preppy stuff.
Sarah: Yeah. It's so hard to figure out who is and isn't a person, because I would've said that J. Crew was some kind of oil magnate safari guy from Connecticut who got into clothes in the 1920s and started off making finch hunting gear. But no.
Avery: Right? Yeah. So the eighties really become this moment where we get multiple trends. The consumer is fully in control, and so preppiness becomes standard. And the interesting thing is then like into the nineties, we see preppy fork off in two distinct directions.
One is business casual. People start just wearing this. Bill Gates is wearing a polo shirt and khakis all the time. And then the other thing we see is Ralph Lauren is on the ascent forever and ever, and you see this rival emerge in the form of Tommy Hilfiger. And there was this movement afoot where kids in Brooklyn would take the train into Manhattan and go to boutiques and steal stuff and develop this incredible sense of style. They started putting clothes together in a totally new way, and it was the origins of what we would eventually call ‘street style’, pairing something expensive with something cheap.
There were these groups of these shoplifter societies called Ralphie's kids, or the Lo Lives, named Lo, like Ralph Lauren, who loved Ralph Lauren. They thought Ralph was so cool, and they were functionally wearing preppy clothes in a really different way. In the Preppy handbook, the stuff was all falling apart and rolled up and disheveled, but they were wearing it in this clean, fresh, that's the whole thing. In hip-hop style. It has to be really clean and different sizing, it's a bit baggier. And it's this whole new way of wearing preppy clothes that Tommy Hilfiger leaned all the way into, he was like, yes, this is the move. And started making streetwear based off of preppy clothes.
And so for a while there's this toe-to-toe rivalry with Tommy Hilfiger and Ralph Lauren. And the interesting thing is that Tommy Hilfiger embraces in a very active way, hip hop artists way before its mainstream in his shows. Sean Combs is modeling in his shows. He's really embracing it, and it should be said that Tommy Hilfiger grows up as this working-class guy. He grew up around people with a lot of different races. He hired people of color at all levels of his company. He wasn't just like throwing this on. He really believed in this. And his brother worked in lighting and music. And so their marketing campaign is to give away Tommy Hilfiger clothes to artists. And they were like, sure enough, someday someone famous is going to wear one of our stuff, one of our things.
And it happened in 1994. Snoop Dog performs on SNL wearing a shirt that says Tommy on it. And they blow up. That's their big moment. And there's this interesting parallel here between the jazz musicians doing their version of Ivy, and hip-hop artists doing their version of preppy. Again, it's not like they're trying to look white. They're taking a sample, they're changing it. And again, they just make this look so cool. If Ralph Lauren took updated Brooks Brothers streetwear updates, Ralph Lauren and Phat Farm, all these brands, all these street wear brands start by looking at Ralph Lauren and Tommy Hilfiger. This is a huge genesis point for this movement.
And then also in the nineties, Abercrombie and Fitch got its rebrand in 1992 and Vineyard Vines started in 1998. It just grows and grows and grows and grows. And then there's this whole other thread happening this whole time that we haven't even talked about. This whole time while this whole American saga has been going on, Japan has been observing it and functionally imitating it and delivering it back to us in the form of Uniqlo, which starts in 1985. The look was mass manufactured by Jewish people. It was made relevant by Black musicians, and it was perfected and modernized by Japanese companies.
I mean, it's like pasta, you can just put anything on it. It's so accessible and legible. You don't have to explain anything. If you're wearing a button-down shirt and a blazer, it's a very friendly look. And that's exactly why it gets exploited by the fascist in Charlottesville and Tucker Carlson. And that's the insidious part of its power, but it also has something beautiful about it, that it is accessible to anyone.
Sarah: And it's one of the kinds of magic talismans in American life where it's as close as you can come to being nondescript. You're not necessarily claiming to have greater class status than you do. But you're also not being marked as low class or untrustworthy by anything you have on.
Avery: Yes, that is so well put.
Sarah: And the more we pretend that we don't have those beliefs in this country, I feel like the stronger they get.
Avery: Yes. Right. And then the other, like the question that I still have in all of this is do the clothes actually matter? Right? If clothes are semiotic, if clothes mean something, but this style of clothing has really become so available and so everywhere, as you said, nondescript while actual inequity, an actual class difference is this gaping chasm then what does it mean anymore? I don't know.
Sarah: Yeah. One of the things, the fashion things, that I've enjoyed in the past couple years is that, okay, so typically if you're a late-night host, you wear a suit. It's just always been that way. It's been grandfathered in at that point. It's weird when you think about it. Whatever. And then we had these lockdown shows, and Seth Meyers never wore a suit again. He came back to the studio, I think has audiences now, and just gave up on the suit. He wears a blue chambray shirt a lot of the time, like he's running a grocery store in Nantucket. Why the suits? And it's just like a little corner that got peeled away and it feels are we now in the era of the late night show host in the chambray shirt? I would like that. And that's also a very preppy moment. It's casual, but it's preppy. It's not disrespectful towards your audience.
Avery: But I feel like that's the key, that is the thing that preppy did. Preppy is the seed that eventually killed the suit. The men on the campus of Princeton developed this so they wouldn't have to wear a suit, and then people wearing business casual in the nineties turned to this look so they wouldn't have to wear a suit. And we're now like finally seeing it come to full fruition, but it's been brewing for a very long time.
Sarah: I think that when this episode comes out, we need to get pictures of ourselves in polo shirts, to celebrate it.
Avery: Do you have, do you engage with the look now?
Sarah: I historically loathe polo shirts because I went to a school that had uniforms when I was in elementary school and middle school. And it was a polo shirt every day for five years. And I guess I associate polo shirts with wearing a school uniform, as I assume a lot of people do if they ever had to wear one. Because that's also such a classic school uniform component for all the reasons we've been talking about this whole time. I feel like this also intersects with the concept of norm core.
Avery: Oh, a thousand percent.
Sarah: And I feel like from the beginning it's been exemplified by what Jerry Seinfeld wore on Seinfeld. Just the whole time, just all of Seinfeld. Very sexually confident guy wearing that.
Avery: Really baggy.
Sarah: Just an aqua mock turtleneck and like really high cut light wash jeans and giant sneakers. Just like, yep. Gonna have some sex today. One of the things I find most intriguing about all this is that when we started talking about preppy fashion and the concept of preppiness, it felt to me like that was a term that you don't hear anymore. You don't hear people really self-describe as preppy, at least not young people. I feel like the last reference to preppiness I heard in a major media franchise was when Noel on Felicity self describes as preppy in like 1999. But it feels like the term didn't survive into the new millennium. But I feel like possibly what you're saying is that it didn't need to because the aesthetic itself had become so ubiquitous that we didn't need to point it out anymore.
Avery: 100%. I feel especially in the early to mid aughts. If something is established enough as a symbol, you don't need to say it. And my pet theory is that, as we've talked about, it's come back in style over and over and over and over again, so many times that almost every generation has grown up with a version of it.
Andre 3000 has this quote that he was like, yeah, I wear these preppy clothes because I grew up in Atlanta in the eighties where everyone was wearing two polo shirts on top of each other and popping the collars. And so he's referencing that. It's always sort of an option.
Sarah: Yeah. I mean, it reminds me of how there was a viral video of a guy skateboarding to Dreams by Fleetwood Mac and Dreams had a moment. But Dreams is never not having a moment, right? It's like always on the radio, there's always people jamming out to it. There's always someone having a breakup or something who's like, ah, Dreams. But there are little moments in the culture where all of us at once will be like, oh my God, Dreams!
Avery: Yes. I mean, the key thing about it is if you think about fashion as not only being something that only young, trendy people engage in, people turn to this look as they age because it looks good on an aging body. You don't have to be thin to wear it.
Sarah: And I'm sure there's that you can look at demographics and like millennials are getting older, we're having kids. We don't want to be like sinking our waists all the time. Are sort of baggy jumpsuits having a moment, because we want to be kinder to our bodies to pay them back for the mid to late two thousands? I don't know.
I want to close by asking you, why is this your magnificent obsession? Because I think this is such an interesting topic, but the world is full of interesting topics. So why do you feel like this has drawn you so much over time?
Avery: Well, in the same way that you can't have a conversation about race without talking about whiteness, and you can't have a conversation about gender without talking about masculinity, I feel like you cannot have a discussion about clothing without this. I didn't even realize, I felt like a fish learning about what water is like. oh yeah, this is the mainstream. When people talk about dressing mainstream or reacting to the mainstream, they're functionally talking about preppy clothes.
And so what is this? Let's name it, where did it come from? How did it get here? And you just can learn. I've learned so much about the course of 20th century fashion just by tracking where this comes in and out. Okay. Wait, but can I give a little tease for the series? There were people who got arrested for dressing preppy.
Sarah: What?
Avery: It's like a huge problem. Yeah. That's the Japan story. It's really interesting.
Sarah: All right. This is a good cliffhanger. Where can people listen to your series, Avery Truffleman?
Avery: Thanks. It's called Articles of Interest, and you can find it wherever you get your podcasts.
Sarah: Thank you so much for coming on. This was so delightful, and I don't know, this feels like kind of a continuation of the Miranda Priestley lesson of it's never just a sweater from a box of stuff. There's always the story of our whole civilization in there.
Avery: Yes. It's just funny. I don't know if fashion is uniquely that way or not, I don't know if fashion does it more so, or less so than any other mass-produced product, but it is the one that we have the most control over. We can choose more readily and more quickly what we wear than like the buildings we live in are the cars we drive. The time scale is just quicker.
Sarah: Yeah. And I think we're more prone to feel like we're expressing our personality and the clothes we wear than in how our cabinets look or whatever. You can see it, you can touch it, you can understand it. You are invested in it because it affects how people perceive you. It's effectively part of your body because how much time do you really get to spend in the world naked?
Avery: Yeah. Yeah, exactly.
Sarah: And yet it's connected to giant forces, way beyond our control that have existed for hundreds or thousands of years. Kind of Creepy.
Avery: Kind of crazy. Kind of beautiful.
Sarah: Thank you so much to Avery Trufelman, our guest. Thank you to Miranda Zickler for editing help. Thank you as always to Carolyn Kendrick, without whom I would be sitting alone in my closet talking to no one. Thank you for being here. We'll see you in two weeks.