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The Grown Woman's Guide to Prep-School Chic

Yes, three years later and we're still taking style cues from 'Gossip Girl.'

Clothing, Footwear, Leg, Trousers, Bag, Textile, Fashion accessory, Outerwear, Street fashion, Style,
Everett

Much like Sex and The City, Gossip Girl—and thus, prep-school charm—has earned a permanent spot in our screen-style hall of fame. If you were just as inspired by the way Blair, Serena, and Little J turned the hallways of Constance Billard into their own personal runway, you're in luck. Here's how to get the preppy look–you know, without looking like you're matriculating.

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1 Mix and Match Opposites
Lauren Perlstein

When you've outgrown the plaid miniskirt uniform, graduate to a knee-length wrap alternative with a striped hem. Pair it with high-heeled wedge tassel loafers, and then make it un-fussy (and totally not Britney-Spears-circa-1999) with sporty details: a baseball cap and a letterman sweatshirt with scrunched-up sleeves.

Old Navy Varsity Sweatshirt, $22, oldnavy.com; Similar Tommy Hilfiger Skirt, $613, luisaviaroma.com; Old Navy Colorblocked Baseball Cap, $14.94, oldnavy.com; Longchamp Pénélope Moccasins, $540, longchamp.com

2 Go for Layers
Lauren Perlstein

To give your favorite fit-and-flare dress a prepster vibe, wear a printed button-down shirt underneath and cuff the sleeves up high. (Match a skinny belt to your cute specs for extra credit.)

Old Navy Classic Patterned Oxford Shirt, $24, oldnavy.com; Old Navy Skinny Faux-Leather Belt, $12, oldnavy.com; Similar Maison Jules dress, $59.99, macys.com; Similar Bar III pumps, $22.25, macys.com

3 It's All in the Details
Lauren Perlstein

Step up a sophisticated collared blouse + cuffed pleated shorts + studded brogues combo with an ultra bright pair of opaque tights. So fresh and simple, right? (Bonus points if you haul around your necessities in a chic reversible tote.)

Old Navy Peter-Pan-Collar Crepe Top, $24, oldnavy.com; Old Navy Cuffed Boucle Shorts (4"), $13.50, oldnavy.com; Old Navy Reversible Faux Leather Tote, $29, oldnavy.com; HUE Super Opaque Tights with Control Top, $15, hue.com; Oxfords & Brogues Santoni shoes. $660, shoescribe.com

4 Try Imperfect Pairings
Lauren Perlstein

The formula for the perfect blend of teacher's pet and classroom rebel: Tuck a V-neck varsity sweater into a pleated knee-length skirt. Pair with dotted socks, two-tone oxfords, and a chic backpack purse. A-plus-plus.

Similar Old Navy sweaters, oldnavy.com; Old Navy Faux-Leather Backpack Purse, $29.94, oldnavy.com; Similar Old Navy socks, $5.50, oldnavy.com; Similar Chinti and Parker skirt, $96.75, theoutnet.com; HUE Ultrasmooth Socks, $7, hue.com; ALDO Flyta Shoes, $90, aldo.com

5 If in Doubt, Go Plaid
Lauren Perlstein

Nothing screams Queen Bee like an is-it-or-isn't-it sheer plaid pussy bow blouse (styled into a traditional men's tie). Keep it dress-code appropriate with skinny trousers and patent lace-up loafers.

Similar Victoria Victoria Beckham top, $475, shopbop.com; Old Navy The Long Pixie Pants, $30, oldnavy.com; Old Navy Faux-Patent-Leather Oxfords, $26.94, oldnavy.com

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