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