The Best Hat for Your Face Shape

Anything with too high of a crown (like a fedora) can accentuate wider cheeks. Instead, opt for one of these flat-topped styles—the structured shape will offset the roundness. (We promise you won’t look like you’re in a barbershop quartet.)

Get the look: Treasure & Bond ($17); Janessa Leone ($286); Gucci ($520)

We know what you’re thinking: Aren’t bucket hats best left to the Delia’s catalog and dads on vacation? Well, the ’90s silhouette is back (and chicer this time, we swear). Both the bucket hat and its relative, the lampshade, are characterized by a downward-sloping brim, ideal for balancing a longer face.

Get the look: Brixton ($58); Pixie Market ($72); Helen Kaminski ($220)

Just as angular shapes flatter round faces, a less-structured shape is best for a strong jawline. (Remember, the goal is to complement your features, not mirror them.) Bonus points for on-trend details like a frayed brim or chunky stitching.

Get the look: LA Hearts ($21); Hat Attack ($98); Filu ($496)

You can pull off a variety of styles, but avoid anything too oversize, which can overwhelm daintier chins. These classic menswear hats have a smaller brim that won’t drown you but will still keep the sun off your face.

Get the look: Banana Republic ($47); Peter Grimm ($65); Rag & Bone ($230)