I wish I had the appropriate clothing to wear with some of the non-casual hats I like best. I kind of look a bit like I'm from another era and while I don't want clothes that look like I'm playing dressup to be a character from another time, I'd like stuff that reflects my looks/personality/tastes for some occasions.
Have you tried poking around thefedoralounge.com forums? I used to browse onto that site every once and while and just recently joined (and stopped lurking,lol!). There's a lot of people there into more vintage and golden era clothes, but also a lot of threads on making things work with more modern style. They've even got a sub-forum just for the ladies.
"People in glass houses shouldn't use Windex when living near bird sanctuaries."- myself
"We are never alone my friend. We are constantly in the company of victories, losses, strengths and weaknesses. Make no mistake, life is war...and war is hell. Those who fight the hardest will suffer the most...but that's what you have to do: Fight. As long as you're feeling pain, then there's hope...because only the dead do not suffer." -RD Metcalf