This Hilarie Burton photo contains
business suit, fedora, felt hat, homburg, stetson, trilby, boater, leghorn, panama, panama hat, sailor, skimmer, and straw hat.
There might also be
dress hat, high hat, opera hat, silk hat, stovepipe, top hat, topper, beaver, pith hat, pith helmet, sun helmet, topee, topi, well dressed person, suit, pants suit, and pantsuit.