This James Franco photo contains
boater, leghorn, panama, panama hat, sailor, skimmer, straw hat, horse wrangler, wrangler, fedora, felt hat, homburg, stetson, and trilby.
There might also be
pith hat, pith helmet, sun helmet, topee, topi, covered wagon, conestoga wagon, conestoga, prairie wagon, prairie schooner, porkpie, and porkpie hat.