Buy It Now: Lightning Bolt, $40
What Douchebags Wear: Frat and/or Bar T-Shirts

Comfort is key when you're sipping mixed drinks poolside, so for those times when you have to wear a shirt, opt for a pocket tee. You can stash your shades in the pocket when they're not on your face, and the broken-in, vintage wash on this Lightning Bolt tee makes it feel like you've had it all summer long.