Hats are quite tricky to wear, but once you find the right one, they can be really easy! Try on a few different types to find the style that suits you best and you feel most confident in. Then stick to that style.
Panama hats and floppy fedora hats are probably the easiest to wear, as they suit most face shapes and are ultra-chic! Panama's are perfect to wear on a sunny day or on the beach, while floppy fedora's are better worn at nighttime or during the winter months.