Buy It Now: J. Crew, $80
What Douchebags Wear: Ill-fitting linen shirts

Don't be one of those dudes in a boxy linen shirt when you hit the bar. This seersucker shirt from J. Crew is cut slim in the body and arms like your other button-downs should be, while the fabric ensures you stay cool due to its breathable nature. Plus, this navy color goes with just about everything.