You'll look best in hats with wide brims, cowboy hats, sun hats, or hats that cut across the forehead, to shorten the potentially exaggerated effect of a long face. Avoid beanies for this very reason.

A squared face has the benefit of strong, angular facial features, which can be overly exaggerated with hats that sport similar angles. To avoid overkill, soften them a bit with floppy or wide brims. A cloche is also a great fit for this distinctive face shape. You'll look best in hats with wide brims, cowboy hats, sun hats, or hats that cut across the forehead, to shorten the potentially exaggerated effect of a long face. Avoid beanies for this very reason.

A person with an oval face enjoys the versatility of choice, as an oval face goes with nearly every style.

If you have a round face you should use a top hat (lengthens the face) and small brim (helps the face look more narrow) with angled cut. Avoid flat hats.

Diamond Shape

For a diamond-shaped face, how you wear the hat may be as important as which hat you wear. Because a diamond face has width around the top part of the head and a narrower jawline,, wearing a hat further back on the head can mitigate the potential for a shortened face. Pick a pull-on you can style further back or something with a shallow crown, like a pork pie