11 Preppy Outfit Ideas Fit for a Modern Blair Waldorf

Preppy style is having a moment, but it’s not quite what you might remember from your school days. With designers like Thom Browne, Simone Rocha, and Giorgio Armani putting their spin on the classic aesthetic, it’s no longer about looking like you just stepped out of a school uniform catalog. Instead, we’re seeing iconic pieces—rugby shirts, ties, and pleated skirts—reimagined with a contemporary twist.

The preppy looks of today aren't exactly the hyper-polished fits spotted on the Met steps in Gossip Girl, but they're certainly ones Blair Waldorf herself would approve of. While the beloved character often stuck to a very specific mold of prim prep with her array of cardigans and headbands, today’s preppy aesthetic has a bit more edge.

Ready to channel your inner Charlotte York? Scroll down for 13 preppy outfit ideas that’ll take you from brunch to the office in style.

Rugby Shirts

The traditional rugby and collegiate shirts of the past are getting a modern update. Simone Rocha’s recent runway look exemplified this, pairing an oversized rugby shirt with feminine ruffles for a soft, romantic twist. The bold stripes and relaxed fit keep the shirt’s sporty roots intact, while the styling introduces a playful edge.

Ties

Once solely reserved for formal events, the humble necktie is quickly becoming the hottest accessory. From the red polka dot style Hailey Bieber wore to Ayo Edebiri's 14-karat gold-dipped feather tie she wore at the Golden Globes, all the cool girls in fashion are wearing ties right now.

Knits

Sex and the City lovers will remember that one of Charlotte York’s signature wardrobe pieces was a good sweater—whether it was a cozy cashmere turtleneck or a delicate cardigan. Knits have long been a staple of the preppy aesthetic, and they're best styled with equally posh staples like pleated mini skirts.

White Button Downs

A classic white button-down shirt styled with a tie and an oversized grey blazer are the perfect pairing. Brighten it all up with a red pop for a fun take on the classic preppy aesthetic.

Collars

Preppy style is also about tailoring, which is why a collar detail is key to achieving the look. Whether it's a barn jacket-style (a favorite of the British royals) leather pop or a pinstripe shirt layered under a sweater, making the collar a protagonist of your look will always help you lean more prep in your outfits.

Layered Sweaters

Layered knit sweaters are a hallmark attribute of the preppy aesthetic that add texture and depth. Why settle for just one knit when you can double up? A lightweight cable-knit over a long-sleeve shirt or a chunky crewneck draped over the shoulders gives it a classic collegiate charm.

Plaid

Plaid has long been a symbol of polished tradition. From crisp coats to skirts, the pattern is endlessly versatile, whether it's a matching blazer-and-skirt set or as a pop of print in a necktie.

Trench Coats

On the runway at Burberry's fall ready-to-wear show, the ultimate preppy designer brand incorporated two crucial staples of the aesthetic: plaid and trench coats. You don't need to wear a classic beige hue to get the same feel; instead, play around with colors and textures.

Pleated Skirts

Pleated skirts have a timeless appeal that has both structure and movement. For Chanel's haute couture spring/summer 2025 show, Kylie Jenner wore a cropped tweed matching set with a mini pleated skirt that felt fresh and classic at the same time. But it can also go sporty, as evidenced by the street style outside the Lacoste fall/winter 2025 show.

Socks

Pairing socks and heels is a key preppy styling trick that gives off schoolgirl vibes. And there's no right way to do it, whether it's a coloblocking version or just an all-black look.

Headbands

In true Blair Waldorf fashion, headbands have been a major source of inspiration that's come out of Fashion Month. And the modern preppy headband is looking more athleisure than posh, with people gravitating toward elastic cotton headbands. From an elegant mini dress to a Penny Lane coat, there's no shortage of how these can be styled.

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