Guess I'm not the best one to ask...Originally Posted by JJWord
In all seriousness, I wear my Fedoras with anything. Well, except my Speedos...that calls for a Panama.
If you get just one lid, I think a Grey is the way to go for all around use. That being said, I'm about to order a black Akubra Homburg (which is not a Fedora, bit it's a suit hat) for picture day. And a Bogart or Stylemaster in a grey as well to mix it up. I think I will like the bound edge for suits...and I can still wear those in everyday clothes...just because I can. Don't concern yourself with other's and what they think...if you think the hat looks good on you, then it probably does. Confidence will come as you wear it.
The Akubra bug has biten me and I figure it isn't going to get any better with the Australian/US exchange rate...so get 'em while they're hot.
Search in the Bogart and Federation threads and you will see many a daper gent wearing suits.
Nonetheless JJWord, you will wish you'd started the fedora gig a long time ago. Do it.
Your mileage my vary Don't run with scissors.