Foppy hats are vintage Fay Dunaway from the 1970's and since 70's style is in right now I'm loving this look. Oversized sunglasses or a pendant necklace go well with a hat like this, but keep it modern lest it look too costume-y.
D&Y (www.davidandyoung.com) wool hat
Fedoras come in a variety of styles. I like this one with a skimpy brim.
Calvin Klein fedora
I love this hat, but it also needs to be worn with modern pieces. No trenchcoats, or you could end up looking like Harriet the Spy.