Heading to a big sports game is the perfect opportunity to show that you can "hang;" so nix the heels and miniskirt. Unless you have serious ties to one team, figure out what team he's rooting for and go with that; it will show you pay attention to him and hey, it makes dressing a little easier. Wear jeans and a cute crewneck sweatshirt or an awesome vintage sweater in his team's colors. Pair with trendy flat, lace-up boots, retro sunglasses and a small bag. Go get 'em tiger!
Sports, beer, and a girl at your side, could it get much better? Show off your manliness in a pair of dark jeans, a long-sleeved t-shirt and fleece jacket. Add a pair of cool, retro kicks and aviator sunglasses and you'll be the epitome of suave.