Style Blair Waldorf would be proud of.
Article by: Julia Benito
Clothing fads are a dime a dozen, but there’s no denying how modern preppy style is very much a staple in fashion. Born from sportswear for polo, sailing, tennis, and rugby, as well as equestrian and nautical detailing back in the early to mid-1900s by the upper class, preppy outfits have since been the quintessential style for top Ivy League schools for their clean, crisp, and sophisticated silhouettes.
Most associated now with the likes of fictitious television characters like Blair Waldorf from Gossip Girl and the rest of the ladies at Constance Billard (including those in the equally fashionable reboot) for their pleated tennis skirts, polo collars, sweaters draped over the shoulders, vests, and checkered accents, preppy fashion has made its way to becoming a beacon of summery, country club chic.
Read on below to see some of our favorite classic preppy ensembles and how you can integrate this classic style into your own wardrobes this 2025 with a mix of affordable and luxury fashion from ZALORA.
V-Neck Sweatshirts
A constant at Constance — no, the Gossip Girl references aren’t done just yet — is a V-neck sweatshirt layered over a crisp button-down. Audrey Hope, played by Emily Alyn Lind, in the Gossip Girl reboot is well known for her use of the oversized, pairing it with either shorts or a skirt for a fun, youthful ensemble — necktie optional, though highly recommended. Get a tad bit edgy with chunky loafers like Audrey or keep it clean with neutrals and trainers. Either way, you’ll be looking certifiably chic.
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Sweater Vests
Sweater vests have had their ups and downs in the fashion scene, being the face of all things “dorky” for quite some time. However, with the pull of preppy fashion resurging, they’ve never looked as good as they have today. Much like their full-sleeved sisters, these sweater vests are great for layering up with collared pieces for the perfect mix of unorthodox and classy.
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Tennis Skirts
Perhaps the pinnacle of women’s preppy outfits, the short tennis skirt is a must for your next cool-girl summer ensemble. Sleek, clean, and versatile, these skirts make wonderful pairings for just about anything — polos, tees, oversized sweaters, cropped tops, etc. Classic white will always be a good start, as it gives you a wide range of color combination options, but don’t be afraid to mix and match with bolder colors.
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Cardigans
When cooler weather rolls through, a cardigan can make for a great statement piece for your preppy look. Layer up with an oversized cardigan, a skirt, and some sheer tights to keep the look balanced, or opt for a cropped cardigan that you can wear on its own for a more modern, body-hugging take.
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Sporty Dresses
While preppy chic does love its layers, sometimes we’d instead go for a one-and-done kind of look. Luckily, with the help of sporty dresses, we can still get that breezy country club vibe with fewer garments. A lovely loose t-shirt dress alongside accents such as baseball caps or bucket caps and trainers is an easy outfit to throw on. Or, if you’re feeling like dialing it up a notch, a sporty tennis dress will do the trick just the same.
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