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