The Evolution of the Preppy Fashion Trend and How to Wear It Today

The 90s preppy fashion is having a major moment.

Collage of preppy clothes, including Princess Diana wearing pink gingham pants and matching sweater, and a person with long brown hair in a ponytail wearing a white tennis skirt and sweater
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Preppy style is having a major moment. Remember the khakis and cardigans of the '90s? They've made their way back into our wardrobes, along with the likes of polo shirts and Mary Jane shoes. American prep style has survived brand bankruptcies (J. Crew emerged from bankruptcy in 2020), store closures, the rise of athleisure, and hype beast trends — it simply evolved to suit a new wearer after each fashion era in which it didn't quite fit.

Ready to dive into the preppy aesthetic? Let's take a look at the evolution of the preppy trend and how you can wear it today.

How It Started

Group of men holding tennis rackets wearing knit sweaters and khaki pants
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Back in the late 1890s and early 1900s, "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 preppy style, and we really never looked back.

The 50s Preppy Style

Collage of women wearing 50s preppy fashion, including cardigans, long poodle skirts and Mary Jane shoes
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In the 1950s, the trend expanded even more. Just think about your favorite movies based in that decade, whether it's Grease or Pleasantville — 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, which were now being worn off-field, 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 as well.

Olivia Newton John in Grease wearing a cardigan draped over her shoulders with a collared shirt
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The 80s Preppy Style

Collage of Princess Diana wearing a knit sweater and pants, along with Brooke Shields wearing a knit sweater with a plaid shirt underneath to represent the 1980s preppy style
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Once we reached the '80s, preppy style as we now know it really began to happen — thanks to a book called The Official Preppy Handbook. Originally, it was meant to be humorous and tongue-in-cheek, but it sold more than a million copies, inspiring people to start wearing khakis, plaid blazers, and knotting sweaters over their shoulders unironically. While these clothes had still 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. Prep was popular, and while going the rocker route was the perfect way to rebel against this buttoned-up norm, we still consider Brooke Shields and Princess Diana — with their turtlenecks and tartan blazers — to be fashion icons of the decade.

The 90s Preppy Style

Collage of 90s preppy fashion, including Britney Spears with Tommy Hilfiger and Dawson's Creek stars Katie Holmes and James Van Der Beek
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The late '90s brought a new, shrunken twist. Pants styles were lower, boot-cuts were in, and Britney Spears turned 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 of Dawson's Creek (in fact, the cast really did appear in a 1998 J.Crew catalogue).

The 2000s Preppy Style

J. Crew fashion show, with a row of people lined up in ponytails, colorful knit tops, shorts and pants worn with colorful heels
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It was in 2008 that Jenna Lyons took her role as J.Crew's creative director and began shaking things up, making us think of preppy style as shockingly bright colors, tons of sparkle, and playful twists. Things became less Nantucket and more fashion-girl approved — and by fashion-girl, we mean even Anna Wintour was a fan. But eventually, another shift occurred, and athleisure made its way onto the scene.

By 2015, the comfy joggers and leggings worn by off-duty models looked more appealing than any type of buttoned-up, and black really was back — which ultimately meant that Lyons' whimsical style was out. She ended up leaving brand 2017.

The "New" Preppy Look

Collage of preppy styles, including a person wearing a rugby shirt paired with striped pants and aperson wearing a cropped sweater paired with khaki pants
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Now, after years of stark minimalism and comfy basics, the preppy style has returned. Back at Fashion Week, collections made as much clear. 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. These styles are on sale everywhere from Urban Outfitters to Everlane, and J.Crew.

Collage of the preppy trend, with one person wearing a blue plaid blazer over a shirt and tie with belted shorts, with another person wearing a brown plaid blazer.
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It appears that things seem to be going in a seasonless direction, and many are investing in capsule collections instead of stocking up on here-today-gone-tomorrow pieces. It's the perfect time for preppy style to shine once again, as basic white button-ups, chinos, stripes, and gingham print are all details that have longevity — and won't look bad with carrot-leg jeans, either.

And, should things change tomorrow, and we all decide that it's time to dress exclusively in bedazzled robes or animal prints? Prep will be ready, shape shifting into knits we can pair with that loungewear, or balancing out the prints with a good ol' neutral. As it has so many times before, it'll simply shapeshift to match the mood — and the market.

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