How to Wear Hats. Hats are often worn out of necessity, but wearing hats as fashion accessories takes courage. The secret is to choose the right hat and wear it correctly and with confidence. The following will help you to wear hats without looking or feeling ridiculous or out of place.
Choose a hat that fits your face and complements your skin color. For instance, a person with a long face shouldn't wear a hat with a lot of height, but a person with a round face will look good in a tall hat. A person with ruddy cheeks will look good in a brown hat.
Restyle your hair. For most hats, it's best to pull your hair back or let it hang down without styling it around your face. A sure route to "hat hair" is to style your hair the same way you do when you're not wearing a hat.
Wear the correct size. Your hat shouldn't come down over your ears or fall off every time you tilt your head. It shouldn't give you a headache or leave a red mark across your forehead when you remove it. If you have to fuss with your hat, it's probably not the right size.
Tilt your hat. Sun hats are meant to be worn on the back of the head; fedoras should be worn down over the eyebrows. Berets should be worn on one side. If the hat you're trying on doesn't look right, try it at a different angle.
Match your hat to your clothes. A fedora will be out of place with a sundress, and a sunhat is inappropriate in winter.
Decorate your hat. Put a pin in the band or use it to attach the brim to the crown. Add feathers, flowers or ribbons.
Choose the right hat for the occasion. Sunhats and western hats are meant to protect your face from the sun, but they aren't right for going to concerts or movies because they might obstruct the view of those behind you.