Have you ever intentionally worn something (shoes, jackets, whatever) that you knew to be hideous, for the sake of wearing something hideous?
My answer: For six years, my favorite pair of shoes was this fluorescent plaid pair of canvas sneakers. They were three dollars for a reason. Looked absolutely horrible, but they broke in well. They lost their courageous battle against decency when the Costa Rican rainforest decided the army ants needed them more than I did.
For my wedding shower, my maid of honor bureinato gave me and my husband a matching set of "Sugar Daddy" shirts as a joke. (We requested prank gifts for our shower.) Because not only are they ugly, but there's two! The background is BRIGHT purple, and there are Sugar Daddy candies patterned all over in BRIGHT yellow and red. We wore them all through our honeymoon, and we still wear them because they're very comfortable.
And I also have a pair of slippers from Hot Topic (again, clearance) that are bright blue and silver glitter. I love 'em, but I can't wear them right now because a) it's cold and b) I just had foot surgery. But oddly, people compliment me on them all the time.