HomeFashion90s Preppy Fashion: How to Rock the Classic Style in 2023

90s Preppy Fashion: How to Rock the Classic Style in 2023

90s preppy fashion: Fashion trends alter day by day with little modification to previous fashion styles. However, some fashions never go out of style, and these are simple and not very complicated. Preppy fashion is one of them, which originates from the Ivy League colleges in the United States. They capture this style in the wardrobes of some elite fashion lovers and trendsetters. They used to wear quality dresses and set trends like preppy fashion, which was a status symbol for other people.

Preppy fashion is simply traditional patterns like clean and straight lines, silhouettes, and old-fashioned designs that look unique in this modern era. These patterns can be on tweed, plaid, or khaki. However, if we mix modern trends with traditional ones, then a more awesome combination comes to the stage that is sort of fun as well.

There are diverse ways that can be implemented to obtain a unique preppy style that we see in diverse movies, fashion, and talk shows. In this article, we will dive into the details of how one can rock 90s preppy fashion in 2023.

The Evolution Of Preppy Fashion

Back in 1934, jeans came into the world of fashion at that time, and with time, college women also got involved in this fashion. Jeans were considered a prime requirement of preppy fashion at that time, and everyone wore them whether they wore a blazer, sweater, or anything else. So let’s discuss diverse fashion trends in diverse decades of the 1990s.

50s Preppy Fashion

In the 1950s, preppy fashion saw significant expansion. Iconic movies of the era, such as Grease and Pleasantville, featured twin sets and sweaters layered over collared shirts, not only on school kids but also in a broader fashion. This period also witnessed the incorporation of sporty rugby shirts into everyday wear, the heightened popularity of plaid designs, the emergence of Americana style with bowling shirts and denim, and a trend towards a tighter, more alluring pin-up look.

80s Preppy Fashion

In the 1980s, the preppy style gained immense popularity, largely influenced by “The Official Preppy Handbook.” Originally intended as satire, the book’s success led to widespread adoption of khakis, plaid blazers, and sweater-tying. Brands like Tommy Hilfiger, Calvin Klein, and Lacoste made preppy fashion accessible. Icons like Brooke Shields and Princess Diana embraced preppy looks.

90s Preppy Fashion

In the late ’90s, preppy fashion took a shrunken and modern twist. Lower pants styles, boot-cut jeans, and Britney Spears popularized the sexy schoolgirl look with white button-downs and pleated skirts. While oversized grunge was a trend, preppy elements like plaid and shirt-tying around the waist remained. J.Crew became a go-to brand for nautical sweaters, and the influence of shows like Dawson’s Creek was apparent in the fashion.

How To Wear 90s Preppy Fashion In 2023

To rock 90s preppy fashion in 2023 while maintaining a fresh and nostalgic vibe, follow these key tips:

Mix and match patterns and colors:

  • Embrace the bold use of patterns like plaid, stripes, florals, and polka dots.
  • Experiment with contrasting or complementary color combinations to create eye-catching looks.

Layer Up:

  • Layering adds depth to your outfit and keeps you warm.
  • You can mix up diverse items like blazers over t-shirts, cardigans over dresses, or vests over hoodies.
  • Complete your overall look by wearing accessories like hats, scarves, gloves, socks, etc.

Add some edge:

  • Inject a touch of rebellion by incorporating grunge or rocker elements.
  • Consider wearing leather, denim, or moto jackets over preppy clothing for contrast and attitude.
  • Swap Mary Jane shoes for combat boots or biker boots for a tougher look.
  • Opt for distressed denim or ripped jeans to add texture and character.

Modernize your accessories:

  • Stay up-to-date by modernizing your accessories.
  • Update your jewelry with items like hoop earrings, chain necklaces, or cuff bracelets.
  • Choose trendy sunglasses such as cat-eye frames, aviators, or round lenses.
  • Trade your backpack or tote bag for a crossbody bag or clutch to match the occasion.


By following these tips, you can effortlessly blend 90s preppy fashion with contemporary style in 2023, creating a unique and fashionable look that captures the essence of the era while staying relevant in the modern fashion landscape.

Outfit Ideas For 90s Preppy Fashion In 2023

Following some advice on how to dress in 90s preppy style in 2023, here are some wardrobe suggestions for various situations:

  • For a casual day out, you can wear a plaid mini skirt with a white button-down shirt tucked in. Layer a sweater vest over your shirt and add some black tights and Mary Jane shoes. Accessorize with a beret hat and a pearl necklace for a chic touch.
  • For a business meeting, you can wear a black V-shaped or turtleneck sweater and then a tweed coat over it. This will look very awesome if you wear quality loafers with it. Also, your pants will be matching, like khaki or any light color. Accessorize with a leather belt and a watch for a polished look.
  • For a date night, you can wear a slip dress with a floral print over a white t-shirt. Layer a denim jacket over your dress and add some ankle boots or mules. Accessorize with some hoop earrings and a crossbody bag for a cute look.
  • For a weekend brunch, you can wear a rugby shirt with a collar and some stripes. Pair it with some jeans and sneakers. Accessorize with a baseball cap and a backpack for a sporty look.

Bottom Line

90s preppy fashion was characterized by a clean, sophisticated look influenced by Ivy League aesthetics. It featured staples like polo shirts, cable-knit sweaters, plaid skirts, khakis, and boat shoes. Icons like Carolyn Bessette-Kennedy and Will Smith popularized the trend. The 80s saw its peak, with “The Official Preppy Handbook” influencing the masses. The late 90s introduced a modern twist, with lower pants, boot-cut jeans, and influences from pop culture, such as Britney Spears. In 2023, the style can be revitalized by mixing patterns, layering, adding edgy elements, and modernizing accessories while preserving the charm of this timeless trend.

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