29. The Everyday Plaid Shirt — Every guy needs a great plaid shirt for fall and winter. They're comfortable but polished, classic but still kind of making their comeback (and trust us, your girlfriends will borrow them, too). Under a wool blazer they're bananas, but they also work with, like, every other thing you own.

Brooks Brothers Tattersall Sport Shirt, $98.50, available at Brooks Brothers; Hamilton The Commerce Plaid Shirt, $245, available at Hamilton.