Preppy Style’s Historic Pathway from 19th Century to Now

Preppy style will never go out of fashion. The staples in fashion, such as cardigans, Mary Janes and polo shirts will never go out of style. American prep has endured brand bankruptcy (J. Crew emerged from bankruptcy by 2020. Store closures, athleisure trends, and hype beast fashions were all factors. What is the secret to staying relevant? Preppy style has evolved to keep up with the times.

The preppy lifestyle has remained a constant throughout the years, from its humble beginnings in 1890s & early 1900s through to its revival in 1980s & 1990s. We still love the preppy look, as evidenced by celebrities like Victoria Beckham, Yara Shhidi and designers such as Chanel and Ralph Lauren.

Are you ready to dive deep into the preppy aesthetics? Before we share some tips on how you can wear this trend, let’s look at the evolution of preppy fashion.

The Origins of Preppy Style

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In the late 1800s and early 1900s the “preppy style” was worn by rich men who attended preparatory or Ivy League colleges, hence the name. Brooks Brothers button downs, knit sweaters and loafers all made up their wardrobe must-haves. By the 1930s college women had also caught on. After the first “Lady Levi’s”, released in 1934 became a staple of preppy fashion, we never looked back.

The 1950s

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The preppy style grew even more in the 1950s. Think about the movies you love that were set during this decade. There are many twin sets and sweaters worn over collared shirts, whether it’s Grease of Pleasantville. And not just on kids.

A few changes also took place at the same time. In the meantime, plaid and sporty rugby shirts were becoming more popular. Denim and bowling shirts created an Americana branch, as did the pin-up style and tighter fitting shirts.

The 1980s

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The Official Preppy Handbook, a book published in the 1980s, was largely responsible for the preppy look we know today. The book was originally meant to be funny and tongue-in cheek, but according to The New York Times, it sold over a million copies. The guide encouraged people to wear khakis and plaid blazers without irony, as well as knot sweaters on their shoulders.

The rise of Tommy Hilfiger Calvin Klein and Lacoste made these clothes accessible to all. Brooke Shields, Princess Diana and their tartan blazers and turtlenecks are certainly preppy icons from the era.

The 1990s

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In the late 1990s, preppy fashion took on a new and shrunken look. Britney Spears made it a big deal to look like a sexy girl in a white button down and pleated skirt. While grunge was a big trend in this decade, some preppy elements were still present, such as plaid shirts and tying shirts around the waist (this time). J.Crew hit its stride with prep in the new millennium style. The nautical rolled neck sweaters were in demand, and people wanted to look like the cast of Dawson’s Creek. The cast did, in fact, appear in the 1998 J. (In fact, the cast did appear in a 1998 J.

The 2000s

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Jenna Lyons, J.Crew’s creative director, began to shake things up in 2008 when she took on her new role. Lyons helped us to think of preppy fashion as a style with bright colors, lots of sparkle and playful twists. Things became less Nantucket and more fashion-girl-approved.

Athleisure was born. In 2015, models wearing leggings and joggers off duty looked more attractive than button-ups. Black was also back.

The “New Preppy Look

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Fashion Week’s collections showed that preppy fashion has undergone a new metamorphosis. Chloe, Michael Kors and Burberry all featured mid-length skirts suits. Versace wore rugby stripes and Versace wore collegiate sweaters. Dior had lots of plaids and neckties. These styles are already on the street, as people are knotting their sweaters again and reaching for a pair of chinos. Collars, vests, and argyle are all back in style.

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. Preppy style is a great choice because it has basic pieces like white button-ups and chinos. It also includes stripes and gingham prints. All of these details are timeless.

Prep will always be stylish–shapeshifting into knits, paired with loungewear, or balancing prints with a good ol’ neutral. It will continue to evolve, as it has done in the past.

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