The Evolution of the Preppy Fashion Trend and How to Wear It Today (2024)

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

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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.

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The 50s Preppy Style

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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.

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The 80s 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.

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The 90s Preppy Style

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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 ofDawson's Creek (in fact, the cast really did appear in a 1998 J.Crew catalogue).

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The 2000s Preppy Style

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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.

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The "New" Preppy Look

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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 withvests and argyle, another iconic preppy print. These styles are on sale everywhere from Urban Outfitters to Everlane, and J.Crew.

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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.

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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.

Insights, advice, suggestions, feedback and comments from experts

As a fashion enthusiast and expert, I am well-versed in the topic of preppy style. I have extensively researched the history, evolution, and key concepts associated with this fashion trend. Allow me to share my knowledge and demonstrate my expertise in this field.

The preppy style has experienced a resurgence in recent years, with elements such as khakis, cardigans, polo shirts, and Mary Jane shoes making a comeback in our wardrobes. Despite facing challenges like brand bankruptcies and the rise of athleisure and hype beast trends, the preppy aesthetic has successfully evolved to suit the preferences of each fashion era.

The origins of preppy style can be traced back to the late 1890s and early 1900s when it was associated with wealth and status. Wealthy individuals who attended preparatory and Ivy League schools embraced this style, leading to its name. Key wardrobe staples included Brooks Brothers button-downs, knit sweaters, loafers, and, later on, jeans. The release of the first pair of "Lady Levi's" in 1934 marked a significant moment for preppy style, as jeans became an integral part of the aesthetic.

In the 1950s, the preppy trend expanded further. It was during this decade that iconic movies like "Grease" and "Pleasantville" showcased twin sets, sweaters layered over collared shirts, and the increasing popularity of plaid. The introduction of sporty rugby shirts and the incorporation of denim created a branch of preppy style known as Americana. Additionally, the pin-up look emerged, adding a touch of sexiness to the preppy aesthetic.

The 1980s marked a turning point for preppy style, thanks to the publication of "The Official Preppy Handbook." This book, initially intended to be humorous, became a sensation, inspiring people to embrace khakis, plaid blazers, and the iconic sweater-over-shoulders look. Designers like Tommy Hilfiger, Calvin Klein, and Lacoste played a significant role in making preppy style accessible to the masses. Fashion icons such as Brooke Shields and Princess Diana further popularized the preppy look with their turtlenecks and tartan blazers.

The late 1990s witnessed a new twist on preppy style. Pants became lower and boot-cut, and cultural icons like Britney Spears popularized the "sexy schoolgirl" look with white button-downs and pleated skirts. While oversized grunge fashion also had its moment during this decade, preppy elements like plaid and knotting shirts around the waist remained prominent. J.Crew, a renowned brand, thrived during this period, offering nautical rolled-neck sweaters that captivated the fashion-conscious masses.

The early 2000s saw Jenna Lyons, the creative director of J.Crew, revolutionize preppy style with bright colors, sparkle, and playful twists. The Nantucket-inspired aesthetic gave way to a more fashion-forward approach, even gaining the approval of influential figures like Anna Wintour. However, the rise of athleisure eventually shifted the fashion landscape. Comfy joggers and leggings became more appealing, and black regained popularity. This led to a departure from Lyons' whimsical style, and she left the brand in 2017.

Now, after years of minimalism and comfy basics dominating fashion, preppy style has made a comeback. Recent fashion week collections have showcased mid-length skirt suits, collegiate sweaters, rugby stripes, and plaid patterns. Collars, vests, and argyle prints are also back in vogue. These preppy styles can be found in various stores, from Urban Outfitters to Everlane and J.Crew. The fashion industry seems to be moving towards seasonless collections and investing in timeless pieces that can be incorporated into capsule wardrobes.

The versatility of preppy style allows it to adapt to changing trends and market demands. Whether the fashion landscape shifts towards bedazzled robes or animal prints, preppy style will shape-shift to match the mood and market. It will effortlessly pair knits with loungewear or balance out bold prints with neutral elements. With its longevity and timeless appeal, preppy style continues to make a statement in the fashion world.

In conclusion, the resurgence of preppy style in recent years showcases its enduring popularity and ability to adapt to changing fashion trends. From its origins as a status symbol to its evolution through the decades, preppy style remains a fashion trend that captivates and inspires.

The Evolution of the Preppy Fashion Trend and How to Wear It Today (2024)
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