The Evolution of Preppy Style — from the 1800s to the 2020s

The 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, per a press release from the retailer), store closures, the rise of athleisure, and hype beast trends. It has never really gone anywhere. Rather, it's simply evolved.

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

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

In the 1950s, the preppy trend expanded even more. Just think about your favorite movies set 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, worn off-field at that time (via GQ), 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

Once we reached the '80s, preppy style as we now know it really began to form — 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, according to The New York Times, inspiring 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 Shields and Princess Diana — with their turtlenecks and tartan blazers — are certainly preppy icons of the decade.

The '90s

The late '90s brought a new, shrunken twist to preppy style. 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 catalog, per Buzzfeed.)

The 2000s

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 — and by fashion-girl, we mean even Anna Wintour.

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 type of buttoned-up, and black really was back.

The "New" Preppy Look

During Fashion Week 2023, 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.

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 like white button-ups, chinos, stripes, and gingham print. These are all details that have longevity.

Prep will always be ready — shapeshifting into knits, we can pair with loungewear or balance out the prints with a good ol' neutral. As it has many times before, it'll simply evolve to match the mood — and the market.