15 Preppy Outfits That’ll Make You Feel Like Blair Waldorf IRL
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Gossip Girl is making a comeback and so is the show’s iconic prepster style. From Blair Waldorf’s statement headbands to Serena van der Woodsen’s pleated school skirt, preppy staples are making their way back into the wardrobes of Upper East Siders and beyond.
If you’re looking to get in on the trend this season, we have you covered. Nailing the style is all about wearing classic, clean pieces, with just a hint of collegiate influence. Stripes in red or blue, penny loafers, and varsity jackets are just a few ivy league items you can incorporate into your everyday look. Ahead, get all the preppy outfit inspo you need to channel your inner Blair.
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Layer a crisp white button-down under a logo t-shirt and add a pop of color with cherry red accessories. Preppy fashion never looked so cool.
What you’ll need: Rotorua, $50, aldoshoes.com
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The Perfect Boyfriend Blazer
Cooler temperatures call for an oversized pinstripe blazer. Pair with a boyfriend-style button-down and an artsy statement belt for an updated preppy outfit that doesn’t feel too stuffy.
What you’ll need: 80’s Wool Tweed Multi Gray Oversized Blazer, $62, etsy.com
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Try wearing your favorite trench inside out, to show off the classic plaid lining. Layer a clear raincoat on top to rev up the cool factor.
What you’ll need: Bhairab Coat, $105, soukandsepia.com
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4
Cher Horowitz-Inspired Plaid
Do Cher proud in a yellow mini straight out of the movie Clueless. Style it up with a graphic knit to bring this ’90s favorite into 2020.
What you’ll need: Motel Wrap Mini Skirt in Grunge Plaid, $48, asos.com
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This outfit is proof that preppy style can take on any vibe – even Victorian goth. Pair up overly preppy items, like a peacoat and button-up, with edgy details, like these leather over-the-knee boots.
What you’ll need: “Classic” Waterfall Wide Collar Coat, $125, rebdolls.com
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Mix sporty and prep, with a color block parka that can do both. This coat can take on any vibe (depending on how you style it) thanks to the super versatile color scheme.
What you’ll need: Cotton-Blend Parka, $60, H&M
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A bold stripe is a trademark preppy look that’ll never go out of style. Try wearing your button-up backwards (yes, backwards) and off the shoulder to make the staple feel brand new.
What you’ll need: Weekday Edyn Organic Cotton Poplin Shirt in Pink and White Stripe, $45, asos.com
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The combo of a red cable knit sweater and jeans is a easy preppy outfit to pull off. Grunge down the look with Docs and a trendy shoulder bag.
What you’ll need: Women’s Crewneck Cable Stitch Pullover Sweater, $24, target.com
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A fitted white turtleneck is a tried and true prepster favorite. You can layer under your favorite sweater, tuck it into high waisted jeans, or double down on preppy vibes with a nautical striped skirt.
What you’ll need: Cotton Turtleneck Tee, $17, Everlane
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Sift through your local thrift store (or raid your dad’s closet) for a retro letterman jacket that gives of allll the preppy feels. Pair with a vintage-y concert tee and contrasting pants.
What you’ll need: Varsity Jacket, $80, GENZ
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A Classic Varsity Sweater
Nothing says “preppy” like a classic Lacoste varsity knit. Try wearing yours oversized with slim joggers or dress it up with a skinny jean and boots.
What you’ll need: Cable Knit V-Neck Sweater, $64, urbanoutfitters.com
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This is the ultimate preppy outfit. An oversized stripe-trim cardigan adds effortless elegance to a white tee and jeans. Keep accessories low-key so the sweater steals the show.
What you’ll need: Tall Boxy Cardigan with Gold Buttons in Cream, $48, asos.com
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A bright cobalt blazer will add just the right about of pop to a neutral outfit. Add some matching sunnies for fashion blogger-levels of chicness.
What you’ll need: Blue Tailored Grandad Blazer, $74, missguised.com
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This is the ultimate cool-girl preppy outfit. Make your classic penny loafers feel fashion-y with cropped jeans and cute striped socks.
What you’ll need: Meze Chunky Fringed Leather Loafers, $56, asos.com
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Red, white, and blue is such an iconic color combination. Try a lipstick red Mary Jane with a dark denim trench for an understated preppy outfit.
What you’ll need: Long Belted Denim Trench Coat, $206, scotch-soda.com
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Hannah Deely
Senior Market Editor, Hearst Women’s Fashion Group
Hannah Deely is the Senior Fashion Editor for the Women’s Fashion Group, where she covers all things fashion and accessories for multiple brands.
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