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Brian Lehrer: Brian Lehrer on WNYC. Now we'll end today's show with our second 100 Years of 100 Things segment of the day. It's thing number 81; 100 years of preppies. The polo shirt, khaki-wearing, loafer-footed crowd you typically find at elite schools and country clubs in the Northeast, particularly preppy fashion. Why? Hidden in the clothes is a story of class, democracy, and the politics of, "Americans' notion of taste." That's according to Avery Trufelman. She's the host of the podcast Articles of Interest, a show about what we wear. A few years ago, she put out a season called American Ivy after falling down the rabbit hole of preppiness while researching for her show. She joins us now to cover the history of this style of clothing, now and as cultural criticism, not just as a fashionista. Hi, Avery, welcome back to WNYC.

Avery Trufelman: Hi, Brian. Thank you so much for having me.

Brian Lehrer: We'll start in the '20s and '30s, 100 years ago on a specific elite campus, Princeton. Why is this the genesis of preppy clothing and its infiltration into our classic dress code?

Avery Trufelman: That's the interesting thing. Next time you look around at what's in all the shop windows, it's a lot of collared shirts, it's a lot of blazers. The style we call preppy or once called preppy is now sort of ubiquitous. There are a lot of early, early hints and origins about where this style that we've come to call classics or normal came from.

All signs really point back to Princeton, which, of all the Ivy League schools, isolated, elite. They have these things called eating clubs, where it's these spaces by students for students. Functionally, a lot of preppy clothes work were workout clothes when you really think about it. They were tennis shirts, polo shirts, and things that you would actually wear to go practice your sport. It was the style that was invented on the Princeton campus.

Today we would recognize it as athleisure. It's the sort of thing you'd wear from sports practice to class, to your eating club, to whatever event you have to do that night. It was a huge source of intrigue, what these elite students were doing on this remote college campus. I think the mystique around it helped spread it out from there.

Brian Lehrer: It's so funny that as you describe it, it's kind of like the things you would do in your sloppiest moments, getting dirty, playing sports, or eating messy food in an eating club became elite dress, dressy dress.

Avery Trufelman: Exactly. That's one of the interesting things about this style. Now we consider these clothes, in hindsight, sort of stuffy, or as you said, country club or elite. At the time, they were so almost outlandishly casual in the 1920s. The way they were worn, the pants cuffed up so that you could slip on your sneakers, the shirt wasn't fully buttoned. It was very, very rebellious when these styles first came out, how deeply casual they were.

Brian Lehrer: Now, moving on in time, you have President Franklin Delano Roosevelt spreading Ivy style to the masses when he signed the GI Bill in 1944. The GI Bill?

Avery Trufelman: Yes. This was a huge moment for preppy clothes. It's really funny to go back and think about this. When the idea of the teenager was new in the aftermath of World War II, it really used to be that there were children's clothes and then adult clothes. Then you enter the workforce and, you start wearing a suit, you leave your boyish sailor suits at home. Then suddenly, in the aftermath of World War II, there was this new era of young adults who didn't necessarily have to fight, they didn't necessarily have to join the workforce. They could enter this realm of life called being a student.

With the rise of the GI Bill, so many people were able to do this thing that they never in a million years thought they'd be able to do, have a college education. For lack of other ideas, the style used to be called Ivy, like the Ivy League. You could go to any major retailer and they'd have a little Ivy section, like, "Here's what you can wear to class. It's something that doesn't make you look like a serious adult, and it's something that doesn't make you look like a little boy."

Then the interesting thing about it is that the style changed with this new influx of students after the GI Bill. These were older students. Many of them were married, had kids, had jobs. They brought elements of real life and a little bit of grittiness onto the college campus. With it, they brought along some elements of their old military uniforms that they liked, such as khakis. That's how khakis became a preppy standard. That's from the military.

Brian Lehrer: Jumping ahead in the timeline again, 1970, the movie Love Story premieres in theaters. This film and the book it was based on, catapulted the word "preppy" into the American lexicon.

Avery Trufelman: [chuckles] Yes. The word "preppy" had always been a derisive nickname for someone who attended a prep school. If you think back to the '70s, this preppy style look is out, out, out. Hippies are in, jeans are in. You would think that this style has gone the way of the buffalo. There is this rise in these nostalgic movies that take place in this idyllic time just before the world got so crazy before everything got turned upside down.

Love Story was one of these movies. I had never seen it before doing this research. I found it very schmaltzy. It was a huge, huge, huge hit. To give you an idea of how popular this movie was, it is often attributed for spreading the popularity of the name Jenny. The main character's name was Jenny. With that, it spread the word preppy as well.

It's about two college students falling in love. One is sort of a rich jerk. The woman in the relationship needles him by calling him Preppy. It took off like wildfire.

Brian Lehrer: Moving ahead in the timeline, 1980, The Official Preppy Handbook was published, a book some listeners might remember, providing everyday people with the secrets of American elite dressing and lifestyle. Also in the '80s, Ralph Lauren took center stage in the golden years of American preppy style. Also, Tommy Hilfiger hit the scene late '80s, early '90s. Hilfiger's target audience was far from those written about in, say, The Official Preppy Handbook. Did preppy clothing become a part of black culture as well?

Avery Trufelman: Oh, in a major, major, major way. Yes, some of it came from Tommy Hilfiger. Tommy Hilfiger realized that there was this intersection with streetwear and preppy clothes, which sounds unlikely. I interviewed some of these guys who grew up in Brooklyn and would just take the train to the Ralph Lauren store in Manhattan and steal stuff. It was part of, to them, what looked elite, what looked fancy, what looked aspirational. A lot of these guys, they call themselves low heads, still continue their passion. Now they buy these clothes, but they still continue their passion for preppy attire today.

Tommy Hilfiger saw this market, saw that young black teenagers were really interested and captivated by this style, and started catering to them, started making cuts that were different, started putting bigger labels on them. It took off. It's like a massive part. Even if you look in the more recent past, when Kanye West used to wear collared shirts in his college dropout phase, it is an integral part of hip hop and street style.

Brian Lehrer: We should say, coming close to the present, that a darker side of preppy clothing in recent years is the convergence between the style and white nationalism. People will recall the tiki torch clan dressed in polos and khakis, chanting, "Jews will not replace us," at Charlottesville in the summer during the first Trump administration, right?

Avery Trufelman: Exactly. That was not an accident. At the Unite the Right march, they thought very, very hard and had a lot of meetings about what they would wear. They chose to wear this approachable look, this friendly look, this institutional look that would make them look like, look like your neighbors. It was this way of announcing, "We are here. We are everywhere. We are all around you." The irony of that, Brian, is that while they're in these preppy clothes chanting, "Jews will not replace us," Jews had a huge hand in making this style popular. Obviously, Ralph Lauren is the most noted example. Even going back to 1902, a lot of the tailors who perfected this style and sold it to college students on campus were Jewish tailors from Latvia and Eastern Europe.

It really is an all-American look in almost every single way. It involves many, many, many different populations in its creation and its history. Of course, it's been co-opted by a lot of modern politics, which is really scary.

Brian Lehrer: In our last minute, nowadays we're still dressing in preppy clothing, but trend names have changed in the last five years. As young people on TikTok will know, there are things called coastal grandma, dark academia, and the old money aesthetic. Here's a funny text from a listener that ties where you started 100 years ago on Princeton in this timeline to today.

Listener writes, "My wife works at Princeton and says that students are more likely to be walking around in their pajamas than anything. The town's Brooks Brothers (preppy store) closed because it couldn't be sustained anymore." Your thoughts?

Avery Trufelman: This style is now a little bit antiquated. I do think it lives on in terms of it's considered nice clothes. Like, what do you wear to go meet grandma? What do you wear on a first date? Now it's considered very nice. The original ethos of it, that sort of casual, careless, wear-it-to-sports-practice, wear-it-to-the-dining-club attitude is very much alive in the athleisure that you see on the Princeton campus today. I think it was a huge mark of American style in the last 100 years. It was how we said, "Okay, we're here. We are wearing these mass-produced clothes and we're casual about it."

Brian Lehrer: That's 100 Years of 100 Things, thing number 81, 100 Years of Preppy Style with Avery Trufelman, host of the podcast Articles of Interest, a show about what we wear. This was amazing. Avery, thank you so much.

Avery Trufelman: Thank you so much, Brian.

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Brian Lehrer: That's The Brian Lehrer Show for today. Thanks for listening, everybody. Thanks for all your calls. Stay tuned for All Of It.

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