If the shoe fits, but looks fucking retarded, don't wear it. At least, so says RW over at Chasing Vincenzo, who's hosting this week's Roundtable.
I'm inclined to agree, with the caveat that, every once in awhile, I like to put on a pair of moonboots and tromp around the apartment pretending I'm on an Apollo mission. My wife hates it when I plant an American flag in the catbox.