Button-down shirts from Old Navy - in classic Oxford White, Splash/Blue Striped, or Plaid Vintage Fit. If it's plaid, button it up and wear it one size too small - underneath it, you've got a classic tee. Maybe it's plain black or maybe it's got a clever slogan. You know the girlies are just dying to find out - as long as you have a good chest. And therein lies the connection between "geek" and "chic".

Under your Penguin All Day Polo in Hillside ($37.99), your Levi's Premium Hesher jeans ($59-$125) are pressed, not worn. (Dorks with dough may choose to go with Evisu Odd Pocket Crochet jeans at $360.) Just make sure they look the same way they did when your mother bought ‘em for you for the first day of school, and leave worn to the bad boys or the jocks.

These rougher fellas she always falls for would have torn the jeans all up by now. That's not your style. You are a safe, sweet, sexy geek boy. Only you know that under your jeans, you're wearing Old Navy's Handsome Devil boxer shorts ($5).

You're all the things that that rough fella isn't; for instance, your Penguin crew-neck cotton sweater ($69) says you're a considerate sorta guy. So her mom's not gonna think twice about letting you in the house to tutor her over milk and cookies. She, in turn, knows you're not gonna dump her for the most popular girl in school.

Maybe you're brave enough to take off your Lacoste Retro Track Jacket ($145). You move a little closer to her at the dining room table, leaning over the books. You smile at her with big puppy-dog eyes and let your Urban Outfitters short-sleeve tee ($14-$24) ask, "Have you hugged my shirt today?" And if things go well, she probably does hug you, at least to say thanks for the tutoring.