If he asks you to watch a football game at the neighborhood pub, you want to look the part while still maintaining your sense of style (read: no oversized team jersey). "A fabulous pair of jeans, great leather boots and a knit vest always work," Bryant says. "They're great for any occasion." Bouwer adds that a fitted sweater finished with a motorcycle jacket is a perfect look for a day date. "If it's cold, wear a draped scarf in a neutral color softly tied at chest level."
Frazer Harrison/Getty Images (left); Rob Loud/Getty Images (right)