this post was submitted on 21 May 2026
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me_irl
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I tried being a hat guy back in my early twenties. Didn't work. Dunno why.
I went through a flat cap/pipe smoking phase. :/
Honestly, not my worst phase, but far from my best.
Gotta go all the way with the handlebar mustache and penny-farthing too.
Lol at first I thought you meant flat BILL hat and was super confused. I wasn't sure if you were an old timey guy who happened to like limp bizkit, or a crackhead.
I think you have to pick a hat type which fits your head shape, but I wouldn't know how to do that. But I think a skinny face would be weird in a bowler hat for example.
This site has nice guides on how to tell your face shape and what hats work well with a given shape