This Matt Dallas photo contains
fedora, felt hat, homburg, stetson, trilby, portrait, headshot, and closeup.
There might also be
boater, leghorn, panama, panama hat, sailor, skimmer, straw hat, dress hat, high hat, opera hat, silk hat, stovepipe, top hat, topper, beaver, pith hat, pith helmet, sun helmet, topee, and topi.