This Hilary Duff photo contains
fedora, felt hat, homburg, stetson, trilby, snap brim hat, 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, street, city scene, urban setting, hip boot, and thigh boot.