According to the fashion experts at About.com, conductor hats work well on round faces, newsboy caps look great on oval faces, floppy hats shorten long faces, and fedoras flatter square and triangular face shapes. Choosing the right hat makes any face shape look better.
Conductor caps look good on round faces because their taller crowns draw the eye upward to even out round cheeks. The newsboy cap puts the focus on the eyes in the center of a pretty oval face. A fedora worn at a quirky angle emphasizes the prominent cheekbones in angular square or triangular faces. A soft knit beanie with a tight fit is a great choice for those with small faces regardless of their shape. The beanie makes a fashion statement and adds interest without overwhelming petite features.