[kerze]

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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.

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mid 30's, not a fatass and balding - maybe I am pulling this off. I bought a fedora last month. The main reason I bought it is that I go for 30 minute walks at lunch with one of my partners and I thought wearing a baseball cap with a suit looked stupid (and because I'm balding and fair skinned I really need a hat if I'm in the sun). Mine is black pinstriped and I have got a few compliments on it. I'm regretting not also buying the tan hat as I think it would go better with my lighter colour suits (or on casual days with khakis).

I was at wine festival back in May with my brother and sister-in-law and we saw a guy who was really pulling off a hat - after some discussion we thought it might have been because he was about 6'4" and that a shorter man couldn't pull it off. I'm 5'9" but I think I'm pulling it off somewhat.