This Ashley Tisdale photo contains
boater, leghorn, panama, panama hat, sailor, skimmer, straw hat, street, city scene, urban setting, fedora, felt hat, homburg, stetson, and trilby.
There might also be
pith hat, pith helmet, sun helmet, topee, topi, business suit, dress hat, high hat, opera hat, silk hat, stovepipe, top hat, topper, and beaver.