15 Preppy Outfits To Channel Your Inner Gossip Girl

Discover timeless preppy outfits for a classic and polished look straight out of the Upper East Side.

When we talk about preppy outfits, it’s impossible to not think of Blair Waldorf and Serena van der Woodsen – the iconic poster children of preppy outfits. In the world of Gossip Girl, it’s all expensive clothing – after all, private schools are exclusive, preppy, and chic.

But preppy fashion isn’t just reserved for the Upper East Side elite; it’s a timeless and versatile style that anyone can embrace. Whether you’re manifesting a future in the upper echelon of society, or simply want to change up your everyday look, preppy outfits offer the perfect blend of elegance and trend appeal.

When you’re ready to channel your inner Blair or Serena, these 15 preppy outfits are a great place to start.

The Cutest Preppy Outfits

1. Ruffled Collars + Plaid

A plaid skirt is a wardrobe essential if you love preppy outfits, as it adds a preppy touch to any look. In this chic outfit, the plaid mini skirt has been paired with a beige sweatshirt, with a little white ruffled collar pocking out the top. Finish with knee-high socks for a high school look.

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2. Monochrome Color Palette

Stick to a monochrome color palette to create a stylish and sophisticated preppy outfit. This look pairs a black V-neck top with a black pleated skirt and a white tweed-style jacket. The all-black accessories, including the knee-high boots and black handbag, help to make the white jacket the statement piece of this outfit.

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3. Cable Knits

Go for a cute and cozy preppy look with this cable knit and mini skirt outfit. The blue, chunky cable knit sweater looks stunning with the navy mini skirt, while the baseball cap, chunky socks, and Birkenstocks add a relaxed and casual touch.

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4. Ivory + Black

Sometimes an outfit is all about how you style it, just like this ivory and black outfit with a sweater knotted over your shoulders, giving the look an instant preppy vibe. To recreate this outfit, you will need a white shirt, ivory smart pants, and sweater, then black accessories, including a black tote and black belt.

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5. Sweatshirts + Pleated Skirt

We love this relaxed preppy outfit, that pairs a sweatshirt with a pleated skirt for a super cute look! This pale grey graphic sweatshirt adds a casual touch to the preppy pleated mini skirt, then you just need to finish the look with black loafers and a black shoulder bag.

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6. Tweed Jackets

Just add a tweed jacket to your outfit to give your look a preppy aesthetic! This pink and white tweed jacket is styled with a black mini skirt, white shirt, and impeccable accessories, including a chunky pearl necklace, a black ribbon at the collar of the shirt, and a bright pink bag – just gorgeous!

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7. Camel Cardigan

This camel cardigan preppy outfit is super easy to recreate at home and is the perfect weekend look! A soft camel cardigan adds a touch of color to the white shirt and white pleated skirt look. Add some cozy knee-high socks and knee-high boots to finish the outfit.

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8. Pops of Red

Stick to a minimalist, neutral color palette then add a pop of color, like red, to create a striking outfit. The red boots and red bow in the hair add a fun pop of color to the neutral white skirt and grey oversized sweater look.

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9. Mini dresses

Style your mini dress with knee-high boots to create a stunning, preppy outfit. This black mini dress features a white scalloped collar, for an extra preppy touch, then is paired with patent boots, and a navy long wool coat to keep you warm during the fall and winter months.

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10. Leather Skirts

Add an edge to your preppy outfit with this striking leather pleated skirt! The black leather skirt when styled with a blue button-down shirt and an oversized grey cardigan, perfectly fits the preppy brief but with a unique and edgy touch. Just add pointed-toe slingbacks and a black top-handle bag to complete the look.

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11. Black + Navy

Black and navy is an underrated color combination that we just adore! Here, a navy sweater has been paired with a black pleated skirt, black knee-high boots, and a black leather handbag. The ruffled collar adds an extra preppy touch to this gorgeous outfit.

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12. Bright green

Don’t be afraid of vibrant colors within your preppy outfit, like this fun bright green tweed mini dress! This pinafore-style mini dress is styled with a white, balloon sleeve shirt to add a little drama and then finished with lots of gold jewelry for a glam touch.

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13. Shorts + Blazer

Keep it simple with this preppy black shorts and blazer outfit that looks super elegant and sophisticated. The black-on-black shorts and blazer are broken up with a white turtleneck sweater, then the outfit is completed with a black handbag, black sheer tights, and black sunglasses.

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14. Black + Grey

A preppy black and grey outfit looks incredible during the fall and winter months – just like the outfit pictured above. Style your black pleated skirt with a black turtleneck sweater and layer a grey tweed jacket over the top to add a preppy touch. Finish off the look with black knee-high boots and a black shoulder bag.

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15. Soft Knitwear

Layer your soft and comfy knitwear over pleated mini skirts when the weather starts to get a little cooler to create a cozy, preppy outfit. This grey mini skirt has been paired with a grey, oversized sweater, a white shirt, and white sneakers for a relaxed finish. The green handbag adds a pop of color to this neutral outfit.

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