How Preppy Became Streetwear

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When Avery Truffelman was a teenager, she bristled at her high school's strict dress code.

It was like, you gotta cover up your shoulders, you got to wear skirts that are a certain length, no writing on your shirts, no jeans.

I think boys had to wear collared shirts.

And the path of least resistance was to just wear preppy clothes, just like do it.

But she didn't like preppy clothes.

I was like, no, I'm going to take the path of most resistance.

And I wore just ridiculous things.

These cowboy boots with this flapper dress and these long hippie beads, just all together, just so I I can avoid looking preppy.

And I just, I did not like the fashion.

I thought it was for rich white people.

It was obliviousness incarnate.

I really did not like it.

And I spent probably my whole youth trying to avoid it.

But as an adult, Avery has given Preppy clothes another look.

Avery hosts a podcast called Articles of Interest that's about fashion and the history and psychology of why we wear what we wear.

And they're doing a whole seven episode season about preppy style.

And I really thought in examining these clothes, I would be going to interview,

you know, old white people in Kennebunkport.

The story is really black, really Jewish, and really Japanese.

So much of like punk style came out of this, street style came out of this.

I promise it's like the weirdest, most interesting topic that you could think of in fashion.

And it's about preppy clothes, which are secretly like the water we are all swimming in.

Preppy style has been around for a long time, though with a different name.

It used to be known as Ivy style.

And obviously, no one calls it Ivy anymore.

And then it morphed into preppy, and now no one calls it preppy anymore.

Like khakis are just pants.

A button-down-collared shirt is just a shirt.

These things have become so basic that we don't even talk about the fact that we're all wearing them.

Did working on this piece,

did it make you want to wear different things?

Oh my god, I'm so into preppy clothes now.

This is Decoder Ring.

I'm Willa Paskin.

The story of how Ivy style spread around the world, morphing, metastasizing, and influencing so much, is the subject of American Ivy, a seven-episode series from Avery's podcast, Articles of Interest.

Those seven episodes are a fascinating, surprising, layered, and intricately connected tapestry that explains how Preppy took over our wardrobes.

On today's show, we're pulling out one of the threads in the series to look at the incredible reach and adaptability of Preppy clothing.

It's a story about the great modernizer of Prep, Ralph Lauren, and how he and his label, Polo, were themselves modernized by customers who helped push Preppy in a whole new direction.

So today on decodering, thanks to Avery and articles of interest,

what happened when Preppy style ran smack into streetwear?

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Avery's gonna take it from here.

Let me start the story the classic way.

Ralph Lauren was born Ralph Lifshitz to Russian Jewish immigrants in 1939.

His dad was a muralist and a house painter who raised his whole family in a two-bedroom apartment.

He grew up in the Moshelu area of the Bronx, which at the time was suburban.

Alan Flesser is a designer and prominent menswear author, and his most recent book is called Ralph Lauren in His Own Fashion.

And of course, he had two older brothers, both of whom were supposed to be very stylish.

Ralph inherited a lot of their hand-me-downs.

They kind of paved the way somewhat.

So Ralph had to figure out how to make his brother's garments work on his body and make them his own.

But Ralph's initial inspiration was not exactly clothes themselves.

A lot of other designers' stories begin with them learning how to sew or poring over their mother's issues of vogue, but not Ralph.

Ralph thought of clothing as a means to an end because his inspiration first and foremost was the movies.

You know, it's the world of Ralph Lauren.

You know, he envisions everything very much like a movie.

Ralph idolized Fred Astaire and Gary Cooper and Carrie Grant, all who paired Ivy style with Hollywood style.

Wearing his sweater over his shoulders, that was Fred Astaire.

Jeffrey Banks is a fashion designer and prolific writer and the co-author of the book Preppy, Cultivating Ivy Style, of which Fred Astair is a titan.

He loved pink and was not afraid to wear pink.

The whole romance of taking his tie and using it as a belt.

That was him.

That was Fred Astaire.

That was Fred Astaire.

Oh.

And a young person looking at a Fred Astaire movie or Carrie Grant who's interested in clothing, pretty hard not to get just eyefuls of ideas about how to wear clothes and how the insider people knew how to put clothes together.

So Ralph ended up thinking cinematically.

At DeWitt Clinton High School, Ralph stood out, dressed in preppy tweeds and sweaters tied around his shoulders.

It was in high school that Ralph changed his last name.

And next to that name, in the 1957 Clintonian yearbook, Ralph Lauren listed his ambition in life.

Millionaire.

He really, certainly in the beginning of his career, he wasn't into the idea of being a fashion designer.

He was the idea of someone who had a certain style that people really respected and liked.

And that was from the very early days, from his working at Brooks Brothers.

Ralph started at Brooks Brothers in 1959.

And Brooks Brothers was the place to be.

Brooks was the place.

I mean, if you could see Fred Astaire at any given day buying Brooks Brothers stuff, it was the fountainhead, really, of American style.

Within the walls of Brooks Brothers was everything a well-dressed man would want to own.

But it wasn't so much the owning of the clothes.

It was more the wear, how you wore them, how you put them together, the nonchalance, so to speak, with which you wore the clothes.

And that was something that you couldn't get from other stores.

It was just an incredible learning place.

Ralph was 20 years old.

He was a salesperson there.

And just standing, you know, in the same floor as all of these well-to-do people and watching how they behaved and watching what they bought was a tremendous formative ground for him to feel like, okay,

I can see this business.

Ralph daydreamed about the kind of clothes he would want to wear, ones that looked more like the movies.

And Brooks Brothers came awfully close, but it wasn't quite what he imagined.

You know, Ralph worked for about a year, a little less than a year at Brooks Brothers.

And I think at the time that he worked there, I think he felt like he got the look.

Now the question was, could he do it any better than what they were doing there?

Ralph realized that the Brooks brothers' clothes were sort of square.

Basically, he liked the soft-shouldered nonchalance of the ivy look, but the cuts were all loose and baggy.

They didn't really have much sex appeal.

They didn't have much shape, you know, they were just boxy and whatever.

Ralph wanted more pizzazz, a little more glamour, and just different proportions.

And Ralph felt that I could give this look, but I could make the clothes fit and feel body conscious, more sexy, which is essentially what he went out to do.

But he could only start small.

So Ralph began with neckties.

Making wider ties.

Like very wide ties, like four inch wide ties, like the kinds Ralph had seen in movies in the 30s.

Ralph decided to name his brand after a sport he had never played.

Polo originated in India, but then it went to Europe and of course could only be played by wealthy people because you had to have a stable of horses because the horses get very tired.

So you'd have to have a stable of horses.

So it was only the very wealthy.

When Jeffrey Banks first encountered a polo tie, he was a dapper little kid in Washington, D.C.

Black kids even then

took, probably took more care about the way they looked.

I mean, I know growing up, there's no way my mother would let me go out of the house not properly dressed, and certainly when it came to church or some event.

And Jeffrey had never seen a tie like this before.

It was different and somehow classic.

It was anachronistic, which is how Jeffrey felt himself.

I always had the sense that I was sort of born in another time.

Always.

I loved old movies and I loved, you know, for when other kids were into the Beatles, I wanted to look like Fred Astaire.

I was about 12 or 13 when I bought my first polo tie, which was $25,

and which I was so incredibly proud of because I thought it was truly like a work of art.

I can describe it to this day.

It was navy and burgundy regimental stripe with a snowflake jack card in between the stripes.

So it was like a tapestry fabric.

And I just thought it was exquisite.

And I remember bringing it home and showing it to my father and being so proud of it.

And he said, well, it's a nice tie.

And I said, no, no, no, it's a beautiful tie.

And he said, how much did you pay for that tie?

And I said, $25.

And he said, $25?

$25?

He said, you don't have $25 worth of neck.

What made this tie so different than other ties?

Well, A, it was wider.

And B, it was in this luxurious fabrication.

It was more luxurious.

I mean, ties were skinnier and thinner

and were not worth talking about, in my estimation.

And this tie had something to say.

In the 1960s, in the swirling, confusing sea of retro fashion, Ralph Lauren had found something that felt like solid ground.

Something that felt classic and sumptuous and all-American, but still looked new.

And you could see it in something as simple as a necktie.

He knew exactly what he wanted when he designed these wider ties.

Because, like a sartorial Rube Goldberg machine, by changing this one thing, it meant you needed to change all the dimensions of everything else.

He needed larger lapels, wider lapels to go with the wider ties.

He needed different kinds of collars on his shirts.

He began something which he's continued to this day, which is he looks at the whole person.

And as polo grew, Ralph wanted consumers to know that all his clothes belonged together, that they were all elements in the cohesive world of Ralph Lauren.

But that's just not how clothing was sold in department stores.

When Ralph and I started out, if you had a collection of clothes, they'd take your trousers and put them in the trouser selection.

They'd put your ties in the tie collection.

They'd put your sport jackets wherever they carried sport jackets, but they didn't put them together as a collection.

By the 1970s, 1970s, Bloomingdale's had become a juggernaut of New York retailers.

The department store was the vehicle that introduced consumers to new designers.

And Ralph wanted to carve out a part of Bloomingdale's entirely for himself.

He specified that all polo merchandise be grouped together within the store.

And no one had done this before.

That was something completely new.

And it meant that he took not just isolated clothes, but he put together a story.

And so it's much easier to get a customer to understand, well, what is Ralph Lauren if you're looking at a collection of clothes that all go together.

So they gave him this first store on the floor of Bloomingdale's.

And of course, once you saw it, it made perfect sense.

Ralph was telling a cohesive story.

So when young Jeffrey Banks heard that Ralph Lauren was coming to DC for a charity fashion show, Jeffrey Banks knew he had to go meet the man.

And I said to my parents, I am not going to school on Friday because I'm going to meet Ralph Lauren.

And I got to the store early in my burgundy double-breasted polo blazer, my polo gray flannels and my polo brown suede shoes.

And at the time, this fandom was very niche.

I mean, the company was very small.

There were maybe 15 people working there.

He had never done an ad at that point.

And a lot of people had no idea who Ralph Lauren was.

But I knew from day one that he would be as big as he is now.

I knew it.

What was he like when you first was he like in his 30s?

He was in his 30s and he was wonderful to me.

Ralph and Jeffrey hit it off.

This Jewish guy and this black teenager talked for two days.

We talked about Fred Astaire and Gary Cooper and Audrey Hepburn and Carrie Grant and Catherine Hepburn and all the things he loved and I loved.

And he said, okay, when you come to look at colleges next year, give me a call.

I might have a job for you.

And that's what happened.

I came up a year later to look at colleges, had my little portfolio of sketches, went up to Ralph's office.

He sat at his desk.

I sat across from him.

And we began talking about Audrey Hepburn and Fred Astaire and Gary Grant and Gary Cooper all over again.

He never once asked to see any of the sketches.

And two weeks later, he called me and told me I had a job.

Of course, Ralph did not care about the sketches.

Ralph has this famous quote, I don't do shoulders, I do worlds.

Which is to say, what he sold to his customers was not the soft shoulders or the hook vent or any of the details or any of the tailoring.

That's not the selling point.

What Ralph was selling was his vision of a complete lifestyle that he was inviting you to enter.

It was like a movie.

And for many people, their first entree into the cinematic world of Ralph Lauren was through a shirt that was once somewhat rare in the United States.

I remember going to Europe, my first trip to Europe, and all my friends said, oh, you're going to Europe, you have to bring back a Lacoste shirt.

It used to be impossible to find knit-collared tennis shirts in the United States.

In Europe, these had been around since 1926 when French tennis player Jean-René Lacoste decided to stop playing tennis in long sweaty dress shirts like all the other tennis players did, and he took up designing his own knitwear.

Lacoste shirts were, again, very rare in the States and often used for actual tennis playing until Ralph Lauren made his version of the shirt.

Around 72, 73, Ralph came out with his shirt.

The Ralph Lauren polo shirt took off almost immediately.

And in 1974, Ralph had another breakthrough when he designed the clothes for the movie, The Great Gatsby.

In this scene, Tom Buchanan is literally on horseback playing polo, wearing Ralph Lawrence stuff.

That was Ralph's breakout movie, put him on the map.

Very, very important for him.

I mean, it was perfect.

Ralph was doing Gatsby-looking clothes to begin with, so it wasn't a stretch, but it's, you know, one of the better clothed, male-dominated movies.

There's still stuff in that that people would wear today.

Ralph, finally, was in the movies, and he continued to lean into his version of cinematic Americana.

His world would expand at every fashion show and ad campaign into Southwestern Cowboy, or Nantucket Sailor, or Colorado Skier, or Rugged Hiker.

When Ralph puts on cowboy gear, he feels like he's a cowboy.

When he wears, you know, tweets, he thinks he's the Duke of Marlborough, you know.

And because he managed to do each of these looks so well,

they really felt genuine.

He didn't go to an Ivy League school.

You know, he went to city college and he didn't even finish city college.

But, you know, when he dressed a particular way, it made him feel like he belonged, you know.

And he put the velvet slippers on with his initials on the front.

And if that made him feel good, that made him

look good and feel good and feel like he belonged to that world.

What's wrong with that?

What's wrong with that?

Ralph's fantasy world became physically manifested when he took over a massive French Renaissance revival mansion in 1983 and converted it into his New York flagship store.

Oh, there's a portrait of the Duke of Windsor on his 12th wedding anniversary.

It almost feels like Epcot in there.

The decor and all the accessories and even the music changes when you leave the preppy section and enter the safari part or the cowboy wing.

It's It's like a Western trading post with statues of buffalo everywhere.

All these worlds are different, but they are all still Ralph.

Like you could take something from the preppy part and mix it with something from the southwestern part and throw on a motorcycle jacket and they'd all work together.

And in the late 1980s and 1990s, a group of kids from Brooklyn would see that, would see what Ralph was making.

And then they would remix and reinterpret Ralph Lauren and Polo for themselves.

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Who the hell knows how to play polo?

What the hell is polo?

Who's got ponies?

Like,

if you understand how he freaked that thing, it was just the perfect, I mean, had he named his line croquet,

would it be around 50 years later?

No.

On any given day, Dallas Penn is usually wearing Ralph Lauren.

There are people that are through and through polo Ralph Lauren collectors.

You among them.

Me amongst, me amongst them.

I am a lowhead.

I am a lowhead.

So lowhead is a big general category.

Anyone can be a lowhead.

You too can be a lowhead if you like Ralph Lauren and you want to collect or appreciate Ralph Lauren clothes.

There are lowheads lowheads all over the world.

But in New York City, there were once very specific crews that were under that banner.

There are Low Lives.

Now, Low Lives is a collective that was formed from two collectives.

They were actually boosting collectors.

A lot of Dallas's classmates in the 80s would just hop on the subway and go to the Ritzy boutiques in Manhattan to steal clothes.

So it was the United Shoplifters Association and Ralphie's Kids.

And they were were from two parts of Brooklyn, Brownsville and Crown Heights.

And they came together to form lowlives.

I wasn't a good thief, but I have friends that boosted.

And my friends that boosted were very good at it.

So for them, me giving them $25 for something that costs $50, that was the deal.

You know, and I bought enough from them that they would charge me even less.

Initially, Teenage Dallas was way more excited about getting good deals on stolen Gucci jackets and exotic exotic foreign designers.

Well, I wasn't really, can I tell you something?

I wasn't super into Ralph like that back then.

Dallas already had some polo stuff, but they were like gifts from his grandma.

Like, okay, I get it.

Grandma wants me to, you know, wear sweaters and slacks and stuff like that.

You know, so I wasn't, you know, was it at that time?

That probably wasn't my jam.

I was probably looking for something more sporty with a little more swag, a little more drip.

And polo was stayed.

But one day in 1986, when Dallas was riding on the subway, he saw another kid about his age wearing something really spectacular.

The first time I encountered it, I was transfixed by it.

I was hypnotized by a kid wearing a jacket.

Dallas couldn't believe that this bright, loud jacket said Ralph Lauren on it.

All I can say is that this jacket, it was like everything around me was grayscale.

But this jacket, all I could see was this jacket.

And I had to have it.

And I ran after him with my friends.

We were going to get this guy's jacket.

Like, not take it from him.

Yeah, we were going to take it from him.

Really?

We were going to take it from him.

When the E-Train opened up and

we ran after him.

He ran up that escalator.

He almost ran up

the rubber handrail.

And we chased him and he got away.

but that was the first time i had ever seen that oh this brand just doesn't make boring stuff this brand's making things that have juz and color and

and like all you know all the sound effects are going off so what i thought was really quiet and boring was in fact not the case so it made me look at the stuff my grandma had given me and like oh wait a minute this is hot this is fire And another thing making Ralph so appealing to 90s kids was MTV.

For a lot of fans, the height of the brand stretches from 87

to 97, roughly.

So the things that were released in that period are touch points because they cross over into music.

And for some people, a Wu-Tang video was like their favorite rap video.

And inside this Wu-Tang video, Rayquan wore this Windbreaker.

Raekwon wore this really brightly colored, sporty Ralph Lauren Windbreaker in the video for the Wu-Tang song, Can It Be All So Simple?

The Windbreaker says Snow Beach on the front of it, and clearly it was supposed to be for like skiing or snowboarding, but Raykwan is wearing it on the street.

He's taking that Ralph Lauren fantasy world and grounding it back into reality.

Here is someone who is looked at as one of the stars, superstars of hip-hop.

And he wore this jacket.

I mean, it's called a Rayquan snow beach now.

Like, Ralph doesn't call it that.

No, Ralph doesn't call it that.

But I mean, that's not his job anyway.

His job is to make it.

And people, they do what they do with it.

If Ralph had updated Brooks Brothers, what updated Ralph was streetwear.

The reason why they call it streetwear, because people saw people on the street wearing it.

This is veteran fashion journalist Terry Aggins.

She started the fashion beat at the Wall Street Journal in 1989 and is sort of a legend.

She says the street style movement had to happen in cities, in places where you could actually see people walking down the street.

wearing clothes in their own unique ways.

You had to have just ordinary people who were out all the times who would save up all their money to buy like a Ralph Lauren polo shirt or a sweater or whatever.

And then they take it and mix it with their jeans, with their cheap jeans that they got of pennies or whatever.

And then they kind of, then they might turn the collar a different way or turn the hoodie or tie a sweater around their waist or they would take it and make it their own look.

It was the same basics, the same collared shirts, just worn in a totally new way.

Hip-hop was like, hey, we're going to freak this sample.

We're going to have you bobbing your head to this song.

And we just took a piece of it.

You know, we just took a, we just sampled it.

And Ralph Lauren at first did not let on that he knew about this new way his clothes were being worn.

Do you know if he knew about like the lowheads and the low lives?

Oh, yeah.

Oh, yeah.

Yeah,

he definitely knows about that.

I mean, I didn't know that was the name for this group, but yeah, absolutely.

Designer Jeffrey Banks used to work with Ralph Lauren.

He did what he's always done, which is stuck to his own vision and stuck to his own style.

Ralph did not intentionally release anything that was meant to look like streetwear.

In the 90s, Ralph did not acknowledge it.

Smart move to not acknowledge it.

Again, this is aspirational apparel.

All right, this is aspirational apparel.

And to be honest with you,

you know, no one's really aspiring to be black.

Not in the way America

would treat you.

No, not like that.

But I mean, it's not like you were trying to look white.

No, no, no.

I was trying to look free.

And when I say this, I mean, what it really goes to is someone who has

total command of their time and resources

i think

uh polo raffle ran has always been made for working class poor people to feel uh a bit of wealth in to feel a bit of kind of a transference from their current economic state.

And what Polo speaks to is lifestyle and the ability to kind of you know do shit on your own terms when you want to who knows how much we spend on polo he probably has an idea he's had to see references to his brand

you know through music had to i don't believe he ever he did not ralph lauren now embraces and acknowledges the lowheads in the brand's history And, like a little wink, Ralph reissued the Snow Beach jacket in 2018, which was was obviously in demand because of Wu-Tang fans and because of die-hard collectors like Dallas.

We'll start with this.

Oh, that's very preppy.

Dallas has a huge collection of Ralph clothes.

Much of it is pristine.

Oh, I mean, this is.

Wait, do you just keep it in the plastic?

This is how it was being stored, yes.

Beautiful knit, beautiful pullover V-neck sweater, 100% wool.

let's turn it inside out this is really the proof in a polo ralph lorrain item when you turn it inside out and you check the seams

let's see how was this built oh this is beautiful

part of the thrill of being a lowhead is slowly amassing all the right elements to create the perfect outfit like Dallas still hasn't found what would really work with that sweater.

I haven't actually worn this sweater yet and this fit.

What am I waiting for?

Probably I need a hat.

The hat would have to be burgundy or navy because it's going to rhyme off of that collar right here.

What do you mean rhyme?

Well, I mean clothing can reference itself with other pieces.

A plaid hit on a hat can reference a plaid collar on a shirt or plaid somewhere else.

So there's

it's about having the items reference and speak to each other and kind of say, hey, yeah, we're not from the same season, but we are all cousins.

We're all family here.

That's rhyming for me.

And that's the particular attraction of Ralph Lauren.

It's because he references his own world and his own past enough times that he's constantly revisiting and reissuing and reworking his own motifs.

You can find a lot that rhymes.

I hold on to Ralph because it does change, but just like the Earth flying around the Sun, when it comes back around,

it's a little different.

But it remembers itself.

It has a thumbprint that repeats itself.

It's self-referential enough where it's like, man, having something from 2022 that connects to something from 1992.

That's, you know, that's a jam right there.

That's a jam.

And when you put them together and other people see the connection, that's the thrill.

For articles of interest, I'm Avery Truffleman.

And for Decodering, I'm Willa Paskin.

You can listen to all seven episodes of American Ivy wherever you get your podcasts, and I really encourage you to do so.

This episode was a standalone story about preppy style, but it was cobbled together from pieces of multiple episodes.

Episodes that I promise tell you a fascinating, big, and surprising saga that spans a century and the globe and hops from Princeton to Japan to punk rock.

You should absolutely check it out and you should check out the rest of Articles of Interest while you're at it.

It is really a kindred show to Decodering and if you like Decodering, I think that you'll like it.

Articles of Interest is created by Avery Truffleman and comes from Radiotopia.

It's edited by Kelly Prime, mixed and mastered by Ian Koss, fact-checked by Jessica Siriano, and has music from Avery, Ray Royal, Sasami, and the Bezelbubs, the Tufts University a cappella group.

Decodering is produced by me, Willip Haskin, and Katie Shepard.

This episode was also produced by Sam Kim.

Derek John is Slate's executive producer of narrative podcasts.

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