It's funny, if you think about the evolution of shorts. They went from grade school gap boxer cool, to the gym short / jean short craze in high school to lame in college and now back to cool in every variety. Here are a few winter shorts to keep the trend going throughout the year!

J. Crew's wool flannel shorts, my top pick:


Gap's tweed wool shorts:And if you want to get crazy, these Mike & Chris Jake leather shorts: