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,; Similar Tommy Hilfiger Skirt, $613,; Old Navy Colorblocked Baseball Cap, $14.94,; Longchamp Pénélope Moccasins, $540,

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,; Old Navy Skinny Faux-Leather Belt, $12,; Similar Maison Jules dress, $59.99,; Similar Bar III pumps, $22.25,

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,; Old Navy Cuffed Boucle Shorts (4"), $13.50,; Old Navy Reversible Faux Leather Tote, $29,; HUE Super Opaque Tights with Control Top, $15,; Oxfords & Brogues Santoni shoes. $660,

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,; Old Navy Faux-Leather Backpack Purse, $29.94,; Similar Old Navy socks, $5.50,; Similar Chinti and Parker skirt, $96.75,; HUE Ultrasmooth Socks, $7,; ALDO Flyta Shoes, $90,

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,; Old Navy The Long Pixie Pants, $30,; Old Navy Faux-Patent-Leather Oxfords, $26.94,

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