Fashion Masochist: Prep School Chic

A year after graduating from my Jackson, Mississippi, private school, I heard the restricted dress code under which I’d suffered six long years would be replaced by uniforms. At first I pitied those who would have to assimilate, but now I’m jealous of those little divas—and the ones over at Ursuline, Notre Dame, and Fontbonne. And I’m not the only one.

Since Gossip Girl debuted last fall, the fashion world has fallen hard for the schoolgirl look. Though one might think a nubile young cast in matching uniforms would excite only those with a certain fetish, the constraints actually inspire creativity. At the fictional Constance Billard, uniforms are personalized with bright tights, flashy flats, layered jewelry, theatrical hair accents, and dramatic capes—at times, all at once. And as the show’s second season premieres this month, preppy collections from Marc Jacobs (plaid jackets), Paul Smith (argyle knits), Luella (over-the-top ribbon headbands), and Dolce & Gabbana (oxford shoes) will pour into stores.

After a daylong Gossip Girl marathon, I’m more than a little primed to get in on the action. At South End vintage shop Bobby from Boston, I’m outfitted in a $400 plaid blazer hailing from 1940s London with a crest on the breast pocket, fabulous enough to make the show’s queen bee, Blair Waldorf, as jealous as that time boyfriend Nate slept with Serena. I pair it with a Peter Pan blouse, flouncy skirt, dark flats, black tie, and wide gold headband.

The ensemble feels great—secure yet a smidge breezy (oh, to pull on gym shorts beneath the skirt for kickball!). I also save the usual 15 minutes spent staring at my closet each morning. But, because I’ll need to wear the blazer again tomorrow, I’m preoccupied with not getting dirty, avoiding messy foods and strenuous activity.

Admittedly, I’m a little old to pass as a real schoolgirl, so in a meeting with my boss, I try extra hard to be professional. He does a good job of ignoring the outfit—yet is there any way to take a twentysomething in a schoolgirl getup seriously? Though I get a leer or two from men, most of the reaction is from the female coworkers who stare, perhaps disgusted by my apparent appeal to the kiddie porn–loving contingent. Lunching at B.Good, I’m handed my burger on a plastic tray, cafeteria-style, and finally feel understood.

My heart says, Bring on the colored tights! But my head knows I’m better off going the more subtle (and versatile) route by rocking preppy separates: a crested blazer with jeans, or plaid trousers with a sleek top. Even so, the next time I see a gaggle of uniformed sophomores giggling over J. P. Licks after school, I can guarantee my jealousy will flare up—like any good Gossip Girl worth her Tory Burch flats.