This The Hills photo contains
boater, leghorn, panama, panama hat, sailor, skimmer, straw hat, fedora, felt hat, homburg, stetson, trilby, street, city scene, and urban setting.
There might also be
porkpie, porkpie hat, dress hat, high hat, opera hat, silk hat, stovepipe, top hat, topper, beaver, hip boot, and thigh boot.