The best way to pick your hat style is to know which hat style suits your face most. For an oblong, long, and narrow face, the best choice may be a cloche, floppy, or fedora hat. People with a square-shaped face may look best in a softer design like a cloche or or a hat with a round or curved crown. Individuals with round-shaped faces should opt for an angular and asymmetric hat style, wide brims, and structured hats.