Streetwear’s Preppy Resurgence Is Just Getting Started

Before I mention the words “city boy” I need to preface for TikTok users that this is not the same type of city boy which Deputy Durland is screaming about in those memes, but the ones from POPEYE magazine.

Launched in 1976, the Japanese magazine printed its slogan “the magazine for city boys” on its first cover, and has spent the last 46 years appeasing city slickers with pages of style that combine streetwear, skatewear, vintage Americana, workwear, and prep.

It’s a glorious combination that brought Japanese and American aesthetics into one succinct look— think preppy overcoats, oxford shirts, and boat shoes with track pants, crossbody bags, and Vans sneakers.

If the look sounds familiar, it’s because it is. While POPEYE editorials have reached cult status with illicit scans being shared on Instagram, the magazine’s unique styling has expanded into the wider menswear space. To put it bluntly, flicking through the pages of Popeye magazine and scrolling through Aimé Leon Dore’s latest lookbook leaves you looking at pretty similar clothes.

It’s no secret that streetwear brands have gravitated towards preppier looks in recent years. With brands like KITH, Aimé Leon Dore, Noah, Dime, Awake NY, Stüssy, Golf Wang and more dropping more dressed-up offerings from cardigans and tailored pants to full-blown suits, it’s clear that streetwear isn’t all hoodies and tees anymore.

Some of this is the brand’s designers and fans growing up, and some of it is part of a wider move towards a new form of preppy style.

Initially born in America’s private schools, the typical uniform worn in these well-to-do institutions includes the typical slim-fitting sherbert-colored shirts, ankle-length chinos, blazers, and, of course, wearing a sweater around your shoulders.

Over the years, preppy style has gained fans far beyond the school walls to become one of America’s lasting influences on fashion.

In Japan, an obsession with the distinctly American look resulted in the influential “Take Ivy” book and had a lasting impact on style there today, as seen in the aforementioned POPEYE editorials. In the US, Black musicians and civil rights leaders took the Ivy look and made it their own.

Fast-forward to the ‘90s and prep was everywhere, with rappers in thick collegiate sweaters shouting out Nautica or Tommy in a song, with the same cultural relevance as today’s Gucci, or Raf name-drops. Finally, Kanye’s College Dropout era in the early 2000s served as a final hurrah for all things prep. Until now, that is.

Like previous iterations of the look, 2022 prep style takes elements of the Ivy League aesthetic and for lack of a better word, messes them up a little.

The new aesthetic is a true downtown-meets-uptown New York mix. Think Columbia students going to the LES, or Ivy League dropouts who decided to transfer to the New School. Similar to the ‘90s take on prep or the pages of POPEYE, the look often veers into baggier and more casual territory than the traditional Ivy tailoring.

The end result today is a red sweater lazily tied around the shoulders of a double-breasted grey blazer accessorized with a NY Yankees cap, as was shown as the fifth look of Aime Leon Dore’s most recent lookbook or Awake NY and Nanamica creating a trio of checkered pieces consisting of a blazer, cargo pants, and bucket hat emblazoned with an imaginary college emblem. Or, anything from our recent fall drop.

The latest evolution of prep is yet to be dubbed with a name (I’m coining the terms city boy 2.0 and Ivy League dropout in the hope that they catch on), and its influence isn’t limited to only streetwear — as is to be expected in the era of new luxury.

You can now enroll in the Kenzo SS23 university with its range of sweater vests, check out what TIER University has on offer at New York Fashion Week, or if you want something from a label that has been at the center of the style since the 80s, Tommy Hilfiger has been digging into its quintessentially preppy archive.

Plus, there is no denying that Tyler, The Creator‘s personal style, with its loafers and knit sweaters, has something of a part to play — and the same goes for A$AP Nast or Blondey McCoy.

Although it will occasionally lay dormant, since the 30s prep has managed to redefine itself and make a comeback through various incarnations. The timing of the comeback makes sense too. Prep is a style made up of classic pieces which have proven themselves to look good, in a time when fast fashion has sped up the trend cycle to such an extent it’s become meaningless, people are yearning for reliable clothes that won’t look embarrassing in a few months time.

Now is just the beginning of prep’s latest manifestation, which means that we’re about to see a lot more than just J-Crew making a comeback via chinos.

It’s time to fasten up your tie and get ready for class, I guess.

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