Face Shapes
This is a guide to help you determine what hat might look best on you. It is full of suggestions to help you shop, but feel free to wear whatever hat suits your style best! If you see information telling you to avoid tall hats for instance, but you like tall hats, try pulling it down low on your forehead to cut down on some of the length. Always try hats on in different ways; pull it down low, push it back to your hairline, put it at an angle. That will help you to see what you like best.
rectangle
Wear a hat pulled down low on the forehead to shorten it and try out Asymmetric, Wavy and Round, upturned brims. The goal is to soften the jawline and avoid adding length to the face. If you like to wear your hat pulled down low, try a hat with a deep crown and curved brim. If you like your hat to sit higher on your forehead, try a shallow crown to avoid adding length. Keep brims mid-length and avoid narrow crowns and stingy brims which accentuate the length of your face. Try wide brims, asymmetric brims, Bowlers, Turbans, Berets and Cloche styles.
square
Wavy brims, curving lines, exposed forehead. The goal is to soften the angular jawline, elongate the face and avoid shortening it by pulling the hat too far down. Avoid mirroring the square, angular contours of the face in the hat. Try a Flat Cap, Wavy or Asymmetric brim style, Cloche with a generous brim, Homburg or Bowler. Keep the brims medium or long with curves and avoid narrow or square crowns and straight or stingy brims. Tilt your hat back on your head to keep the forehead open, lengthening your face.
OVAL
You can wear a variety of styles and brim lengths. If you like to wear your hats pulled down low, try hats with a deep crown. If you like to wear your hats higher on your forehead, try a shallow crown to avoid adding length. The crown should never be narrower than the cheekbones. Wearing a hat tilted forward helps shorten the forehead. Round brims help to add width. The goal is to avoid lengthening and to maintain balance. Try a Turban, Cloche, Fedora, Asymmetrical brims or just about anything really!
HEART
The heart shape is widest and the forehead with round cheeks and a narrow jawline. A very petite face.
With this shape the key is not to overwhelm the face. Wide brims will enhance the wideness of the forehead and cheeks, so try shorter brims. You would look nice with all varieties of caps, a fedora with a short brim, cloche and bucket hats. You can wear lots of styles as long as the brim doesn't overwhelm your face.
DIAMOND
Mid-length brims are best, avoid anything too wide as it will accentuate the pointed chin. Avoid mirroring the pointed chin with a pointed top. Try Fedoras and flat top hats like Porkpies that are tapered and not too boxy. There is a sweet spot here, not too wide and not too narrow.
CIRCLE
Creating length is the goal here, so go for big and tall. Avoid styles that sit too close to the face and head and accentuate roundness. Offset the circular contours of the face with a Fedora or Porkpie that is deep and wide. Try Asymmetrical and Wavy brims. Keep brim length medium or long and avoid stingy brims.