Gant Rugger Doubler Sweater
Buy It Now at Urban Outfitters, $100

A.P.C. Army-Style Bomber Jacket
Buy It Now at A.P.C., $385

Women like when you’re thoughtful about your clothes, but we don’t want you to obsess over them. Know where a label lands on the douchey/awesome continuum, but don’t go out of your way to broadcast your choices. Anything monogrammed or plastered with logos is a no. As a rule, avoid any item with a big label on it, and don't brag about how much you paid for it. It’s a rare girl who cares what designer you're wearing, and if you talk about how long you lined up for that limited-edition Japanese sweatshirt, it might be time to find another selling point.