Buy It Now: GANT Rugger, $175
What Douchebags Wear: Thin V-neck sweaters with logos

Remember when Kanye West rocked this awesome Acne mint green sweater? Yeah, classic kit right there. This version from GANT Rugger costs much less but looks just as cool. Made from 100% cotton, it isn't itchy like wool and won't pill like cashmere—and it's light enough to wear on breezy spring days and summer nights. Throw it on over a T-shirt or polo to go incognito with the preppy crowd. Just please, please don't tie the sleeves around your neck.