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 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.