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I was bored and stuck in suburbia, so I went to the mall. I wandered into a hat store and ended up buying a classic-style hat with a brim popped in the back and straight in the front similar to this:
I was happy with my purchase until I spotted similar hats in a Hot Topic as I walked by. I'll wear it regardless, but I'd like to know if I'm going to look like an attention-starved, douchy twenty-something. Does it depend on what else I'm wearing?
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It's wholly dependent on age, body-type and hairstyle. If you are young, do not wear! You look like Molly Ringwald or Backstreet Boys, depending on your hips. If you are fat, do not wear! You'll look like you're trying to be "That guy" to cover up for being a fatass. If you have an asston of hair, do not wear! You will look like Molly Ringwald.
Once you hit your 30's and you aren't a fatass and you don't have George Michael's WHAM! hair -- you can pull these off pretty easily.