10 Preppy Outfits That Are Even Cooler Outside the Classroom

Put some prep in your step.

Preppy fashion, though classic, is constantly evolving. Whether it's the rugby shirts and denim of the '50s, the button-downs and blazers of the '80s, or '90s pleats and slacks, this aesthetic exudes an undeniable level of cool while also being fun to style. All you really need to put together a preppy outfit is one or two canonically preppy pieces.

Tennis skirts, V-neck sweaters and sweater vests, blazers, and polo shirts are some of the most famous pieces of prep clothing, but there are also fabrics and patterns that are instantly recognizable as prep-approved: plaid, argyle, stripes, and almost anything cable knit or pleated also falls into the preppy outfit category.

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

Once you've identified your favorite preppy essentials, it's easy to mix and match them for an endless array of preppy outfits. To get you started, we've rounded up 10 'fits from modern takes to vintage-inspired, that'll definitely put a bit of prep in your step.

Pretty Pleats

Tennis skirts are a preppy staple. You can lean into the prep vibes by adding a polo shirt and cardigan tossed over your shoulders or opt for sportier energy with a tank top or camisole.

Related: 13 Ways to Wear a Tennis Skirt Off the Court

Striped Separates

Mixing and matching preppy textures and patterns is one way to create a prep 'fit without abandoning your own personal aesthetic. Case in point: a cable-knit v-neck sweater worn with striped green shorts and metallic flats delivers prep with a twist.

Keep It Collegiate

Celebs like Taylor Swift and Gigi Hadid love a collegiate crewneck moment and so do we, but if you're not quite ready to show school spirit, you can create the same prep effect with a letterman style jacket. Any soft jacket with contrasting leather sleeves fits the bill and gives a casual 'fit a vintage preppy vibe.

Related: Taylor Swift Just Wore the Preppy Trend That Gigi Hadid and Dua Lipa Are Fans of, Too

Try a Tie

Add a bit of classic prep school energy to your next preppy fit by pairing a tie with a plaid skirt. You can keep the look from skewing too academic by choosing statement accessories.

Untuck Your Shirt

There's something deliciously undone about an untucked button-down shirt, especially when it's worn under a cableknit sweater. Toss a pleated skirt into the mix and you've got a 'fit that captures the effortless coolness that makes preppy fashion such a standout.

Remix a Rugby

Like many wardrobe staples swallowed up by the prep aesthetic, rugby shirts seen in preppy outfits usually stick to a nautical (blue and white) or jewel-tone color palette, but that's no reason not to mix things up. A brightly colored rugby shirt plus a pair of matching bike shorts is a great take on an old classic.

Pull on a Polo

A polo shirt can make almost any 'fit into a preppy 'fit, but you don't have to return to the dreaded double-layer polo style of the Y2K era. Instead, try an oversized polo with a flowing maxi skirt for a modern preppy vibe.

Related: The 18 Best Polo Shirts of 2023 That Are Both Classic and Trendy

Try Prep Sweats

Who says preppy can't be comfy? The next time you feel like rocking sweats, add a blazer, a baseball cap, and a crewneck sweatshirt tied over your shoulders in classic prep fashion.

Bring a Blazer

With the right blazer, all you need is a pair of striped crew socks and Mary Janes and you've got yourself a complete preppy outfit. If you prefer more coverage, a simple slip dress worn underneath offers the same effect.

Opt for Argyle

The prep aesthetic has always brushed shoulders with activewear, but you don't have to wear a tennis skirt to get in on the trend. Instead, try a matching skirt set in a preppy print like argyle.

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