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Thinking about getting a trilby

I've never worn any sort of dress hat, but I'm a big fan of the trilby.

Anyone have tips on where to buy them?

I'm 23 yrs old, will my friends and people my age think I'm pretentious for wearing one?
 
I think you will be OK in the fashion stakes as traditional head gear (at least here in the UK) is in the fashion shops right now. The other day I noticed trilbies and flat caps by Failsworth in the Top Man store. Me and my dad have been wearing Failsworth caps for decades:001_tongu:001_tongu so at least now we can be trendy.

If you don't feel ambitious enough to try the trilby then a tweed flat cap is excellent, it will keep your head warm, keep sun and rain off your face and can be folded and stuffed into a coat pocket when not in use.
 
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