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Preppy style is timeless.Cardigans, polo shirts, and Mary Jane shoes—all staples of the fashion—will never truly go out of style. American prep style has survived brand bankruptcies (J. Crew emerged from bankruptcy in 2020, store closures, the rise ofathleisure, and hype beast trends. Its secret to remaining relevant? Preppy style has learned to adapt and evolve with the times.
From its not-so-humble beginnings in the 1890s and early 1900s to a revival in the 1980s and 1990s, it's evident that the preppy lifestyle isn't going anywhere. Even today, we still love preppy style—as evidenced by celebrities such as Victoria Beckham and Yara Shahidi, as well as designers like Chanel and Ralph Lauren.
Ready to take a deep dive into the preppy aesthetic? Let's take a look at its evolution before we give you tips on how to wear the trend.
The Origins of Preppy Style
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Back in the late 1890s and early 1900s, the "preppy" style was a sort of status symbol worn by wealthy guys who went to preparatory and Ivy League schools—hence the name. Brooks Brothers button-downs, knit sweaters, and loafers were all part of their closet must-haves. And by the 1930s, college women were in on it too. Once the first pair of "Lady Levi's" were released in 1934, jeans became a major part of preppy style—and we really never looked back.
The '50s
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In the 1950s, the preppy trend expanded even more. Just think about your favorite movies set in that decade. Whether it'sGreaseorPleasantville,there are so many twin sets or sweaters styled over collared shirts—and not just on school kids either.
At the same time, a few changes were happening.Sporty rugby shirts, worn off-field at that time, were thrown in the mix, while plaid became even more popular. Bowling shirts and denim created a branch of preppy called Americana, and there was also that whole tighter, sexier, pin-up look happening too.
The '80s
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Once we reached the '80s, preppy style as we now know it really began to form—thanks to a book calledThe Official Preppy Handbook. Originally, it was meant to be humorous and tongue-in-cheek, but it sold more than a million copies,according toThe New York Times. The guide inspired people to start wearing khakis, plaid blazers, and knotting sweaters over their shoulders unironically.
While these clothes had been a sign of privilege in the '50s, they were being made for the masses now, thanks to the rise of Tommy Hilfiger, Calvin Klein, and Lacoste.Brooke ShieldsandPrincess Diana—with their turtlenecks and tartan blazers—are certainly preppy icons of the decade.
The '90s
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The late '90s brought a new, shrunken twist to preppy style. Pants styles were lower, boot-cuts were in, andBritney Spearsturned looking like a sexy school girl—complete with a white button-down and pleated skirt—into a major thing. Plus, while oversized grunge definitely had a moment during this decade, you can argue that some preppy elements—like all the plaid and knotting shirts (this time, around your waist) were still there. It was prep, new millennium-style, and J.Crew was hitting its stride. People wanted those nautical rolled-neck sweaters and envisioned themselves looking like a cast member ofDawson's Creek.(In fact, the cast really did appear in a 1998 J. Crew catalog.)
The 2000s
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Jenna Lyons took her role as J.Crew's creative director and began shaking things up in 2008. Lyons made us think of preppy style as shockingly bright colors, tons of sparkle, and playful twists. Things became less Nantucket and more fashion-girl-approved.
Eventually, another shift occurred, and athleisure arrived on the scene. By 2015, the comfy joggers and leggings worn by off-duty models looked more appealing than any button-up, and black really was back.
The "New" Preppy Look
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DuringFashion Week, collections made it clear that the preppy style has gone through yet another metamorphosis. Shows like Chloé and Michael Kors featured mid-length skirt suits; Burberry had collegiate sweaters; Versace broke out the rugby stripes; and Dior included a ton of plaid and neckties. Those styles have already hit the streets as people are back to knotting their sweaters and reaching for pairs of chinos. We're seeing collars again, along with vests and argyle, another iconic preppy print.
Final Thoughts
If you want to take your wardrobe in a seasonless direction, invest in capsule collections instead of stocking up on here-today-gone-tomorrow pieces. That's where preppy style shines because it's got basics likewhite button-ups, chinos, stripes, and gingham print. These are all details that have longevity.
Prep will always be stylish—shapeshifting into knits, paired with loungewear, or balancing prints with a good ol' neutral. As it has many times before, it'll simply evolve to match the mood—and the market.
