15 Preppy Outfits That Will Bring Out Your Inner Gossip Girl

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Explore classic preppy outfits that exude timeless elegance and a polished aesthetic, reminiscent of the Upper East Side.

When we think of preppy outfits, it’s hard not to picture Blair Waldorf and Serena van der Woodsen—the ultimate icons of preppy fashion. In the world of Gossip Girl, the style is all about luxury—after all, private schools epitomize exclusivity, sophistication, and chic fashion.

However, preppy fashion isn’t limited to the elite of the Upper East Side; it’s a timeless and adaptable style anyone can adopt. Whether you’re envisioning a future among the social elite or simply looking to refresh your daily wardrobe, preppy outfits strike the perfect balance between sophistication and modern trends.

If you’re ready to tap into your inner Blair or Serena, these 15 preppy outfits are a perfect starting point.

1. Camel Cardigan

This camel cardigan preppy outfit is incredibly simple to put together at home and makes for an ideal weekend ensemble! A soft camel cardigan brings a hint of warmth to the white shirt and pleated skirt combination. Complete the look with cozy knee-high socks and knee-high boots for a stylish finish.

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2. Monochrome Color Palette

Maintain a monochrome color scheme for a classy and refined preppy outfit. This ensemble combines a black V-neck top with a black pleated skirt, topped off with a white tweed-style jacket. The all-black accessories, from the knee-high boots to the handbag, allow the white jacket to stand out as the focal point of the look.

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3. Black and Gray

A preppy black and grey ensemble is perfect for the fall and winter seasons—just like the one shown above. Pair a black pleated skirt with a black turtleneck sweater, and layer a grey tweed jacket for a polished, preppy vibe. Complete the outfit with black knee-high boots and a black shoulder bag.

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4. Black with Navy

Black and navy make for an underrated color combination that we’re absolutely in love with! In this look, a navy sweater is paired with a black pleated skirt, black knee-high boots, and a black leather handbag. The ruffled collar adds a charming preppy detail to this stunning outfit.

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5. Ivory with Black

Sometimes, it’s all in the styling, like this ivory and black ensemble featuring a sweater casually knotted over the shoulders, instantly adding a preppy touch. To recreate this look, you’ll need a white shirt, ivory tailored pants, and a sweater, paired with black accessories such as a black tote and a black belt.

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6. Mini Dresses

Pair your mini dress with knee-high boots for a chic, preppy look. This black mini dress is accented with a white scalloped collar for an extra preppy detail, and is styled with patent boots and a navy long wool coat to keep you cozy during the fall and winter seasons.

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7. Ruffled Collars with Plaid

A plaid skirt is a must-have for any preppy wardrobe, instantly elevating any outfit with a classic preppy flair. In this stylish ensemble, the plaid mini skirt is paired with a beige sweatshirt, featuring a peek of a white ruffled collar for added charm. Complete the look with knee-high socks for a classic high school vibe.

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8. Shorts with Blazer

Keep it sleek with this preppy black shorts and blazer ensemble that exudes elegance and sophistication. The black-on-black combination is balanced by a white turtleneck sweater, and the outfit is finished off with a black handbag, sheer black tights, and black sunglasses for a polished look.

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9. Sweatshirt with Pleated Skirt

We adore this laid-back preppy outfit, which pairs a sweatshirt with a pleated skirt for an effortlessly cute style! The light grey graphic sweatshirt gives a casual vibe to the preppy pleated mini skirt, and all that’s left is to complete the look with black loafers and a black shoulder bag.

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10. Soft Knitwear

When the weather cools down, layer your cozy knitwear over pleated mini skirts for a warm, preppy look. This grey mini skirt is styled with an oversized grey sweater, a white shirt, and white sneakers for a laid-back vibe. A green handbag adds a vibrant pop of color to the neutral tones of the outfit.

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11. Tweed Jackets

Elevate your outfit with a tweed jacket for an instant preppy vibe! This pink and white tweed jacket is paired with a black mini skirt, white shirt, and perfect accessories, including a chunky pearl necklace, a black ribbon at the shirt collar, and a vibrant pink bag—simply stunning!

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12. Leather Skirts

Give your preppy outfit an edgy twist with this bold leather pleated skirt! Styled with a blue button-down shirt and an oversized grey cardigan, the black leather skirt adds a unique flair while still fitting the preppy aesthetic. Complete the look with pointed-toe slingbacks and a black top-handle bag.

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13. Bright Green

Embrace bold colors in your preppy outfits, like this playful bright green tweed mini dress! The pinafore-style dress is paired with a white balloon-sleeve shirt for added flair, and topped off with gold jewelry for a glamorous finish.

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14. Pops of Red

Keep it simple with a minimalist, neutral color palette and add a bold pop of color for a striking outfit. The red boots and matching red hair bow bring a playful touch to the neutral combination of a white skirt and oversized grey sweater.

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15. Cable Knits

Opt for a cute and cozy preppy style with this cable knit and mini skirt ensemble. The chunky blue cable knit sweater pairs beautifully with the navy mini skirt, while the baseball cap, chunky socks, and Birkenstocks give the outfit a relaxed, casual vibe.

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There you have it—15 preppy outfit ideas that will bring out your inner Gossip Girl in no time. From timeless plaid skirts to chic blazers, these looks are perfect for adding a touch of Upper East Side flair to your wardrobe. So go ahead, mix and match, and let your style speak volumes—because, as we all know, fashion is the ultimate power move.