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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1

Cool in Crimson

Street Style - Mercedes-Benz Fashion Week Australia 2016

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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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2

The Perfect Boyfriend Blazer

Street Style : Paris Fashion Week - Womenswear Spring Summer 2020 : Day Nine

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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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3

A Posh Plaid Trench

Street Style - LFW February 2018

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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

Street Style - LFW September 2018

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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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5

Gothic Peacoat

Street Style: Day 4 - LFW September 2017

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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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6

Prepster Parka

Street Style - LFWM June 2018

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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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7

Red and White Stripes

Street Style - Day 1 - Stockholm Fashion week Spring/ Summer 2018

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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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8

Vintage-y Cable Knit

Street Style : Paris Fashion Week - Womenswear Spring Summer 2020 : Day Nine

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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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9

Clean White Turtleneck

Street Style : Paris Fashion Week Womenswear Spring/Summer 2018 : Day Four

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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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10

Varsity Jacket

Street Style: February 27 - Milan Fashion Week Fall/Winter 2016/17

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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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11

A Classic Varsity Sweater

Street Style : Paris Fashion Week - Womenswear Spring Summer 2020 : Day Nine

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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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12

Nautical Cardigan

New York Fashion Week - Street Style - Day 2

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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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13

Bold, Bright Blues

Street Style - Duesseldorf - August 2017

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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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14

Updated Penny Loafers

Street Style - September 2016 New York Fashion Week - Day 6

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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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15

Updated Trench

Street Style : Day One - Paris Fashion Week Womenswear Fall/Winter 2017/2018

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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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