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:
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