If it's not your usual style it might take a little getting used to, but I also think it really suits you. In fact, I think it goes so well with your handlebar moustache and haircut that you could step into a historical photo and blend in perfectly (similar to what LuvMyMan suggests above)!
Alden 403 Moc Toe Boot - Brown Chromexcel - $680 The classic "Indy" style Alden Boot in the classic Horween brown Chromexcel. 
Grant Stone Diesel Boot Dark Olive Chromexcel - #395 Goodyear welted, Horween Chromexcel, classic good looks. 
Himel Bros. - The Ross Mk. 1 Leather Jacket Classic D-pocket motorcycle/aviator style jacket. 
The image, we see in the mirror, is far from always congruent with the image of you, other people see. You may not see yourself quite like we do(?)
Personally, I can't imagine a face, that would look more at home below that hat. It's so close to absolutely perfect ... an obvious keeper! I'm sure, you will grow to love it - but the call is entirely yours
Just picked up this chocolate brown Whippet VITA-FELT a couple of days ago. It's in excellent condition but did require quite a bit of steaming. It has a 2 1/2" brim with 3/8" burnt orange grosgrain edging and a 5 1/2" open crown which is wrapped in a 1 1/2" matching burnt orange grosgrain ribbon. The ribbon is a little fancier than the other whippets I own. The crown tip says Vita Felt. The silk liner is a little loose but that's an easy fix. The leather sweatband is unreeded. The red Stetson tag behind the sweat has "702 1/2" stamped on it. I guess that's the block. I don't think I've seen that number on any of the Stetsons I own. I'm thinking the hat dates from when Stetson first introduced VITA-FELT.
Thank you John.
The original hatband wasn't in the pictures, so I didn't know how it was, it only showed the feather hatband. I got it for the binding and this was a surprise
