How To Choose A Hat For Your Face Shape, According To An Expert

For me, a hat is like a unicorn—it’s a beautiful, mystical creature that I’ll always admire, but too afraid to touch if/when given the chance. (I guess it’s a good thing I’m not a royal.) Don’t get me wrong, I absolutely adore hats. But, I can’t seem to find one that fits me just right thanks to my round face shape.


Sound familiar? Don’t give up just yet. There is a way to find a flattering, statement-making hat for your face shape, you just need to know what to look for. That’s why we called in a hat expert from, Jennifer Boughton.


“Many people are unaware that a hat isn’t just a hat—a hat needs to fit your look to a tee, starting with your face shape,” Boughton says. “There happen to be five types of face shapes, and all of them, with the exception of one, have a few distinct hat styles that will suit them best.”


Whether you’re searching for a new beanie to keep you warm this winter or you’re interested in adding a little flair to your outfit with a brand-new fascinator, here’s how to find the most flattering hat for your face shape. 


Round: A Flat or Ivy Cap

“A round face practically begs for a hat with a decorative crown, that is at least as wide as the face,” Boughton explains. “A flat or ivy cap is ideal for a round face.”



Isabel Marant Velvet Ha



Gabor Wool Herringbone Flat Cap


Heart-Shaped: Cloche or Pillbox

“If you have a heart-shaped face, you’re best off with a classic pillbox, cloche, or medium brim fedora,” Boughton adds. “That’s because a heart-shaped face is in danger of emphasizing a wider forehead—so avoiding too large a brim is important.” 


Felt Textured Cloche Hat



Edina Pillbox Hat


Square: Bowler or Beanie

“Sharp jawlines look best with more of a rounded or asymmetrical style,” Boughton says. “If you have a strong set square jaw, you’ll bring out your best advantage in a bowler hat, beanie, or even a center dent fedora.”


Bowler Hat



Honeycomb Cashmere Beanie


Oblong: Beret or Wide-Brimmed Hats

“If you have a long face shape, you’ll want to avoid adding too much height to the face or head,” Boughton says. “Instead, opt for wide brims, or something that covers the forehead, in order to even out the length of the face. A beret, or anything with a wide brim, will work with this face shape.”


Leather Beret 



Star-Print Wool Felt Beret


Oval: Literally Any Hat

“There’s one face shape that will adapt to virtually any hat,” Boughton says. “The lucky accessory lovers with oval faces are unlimited in their hat choices. Our oval-faced friends should follow this tip: Make sure your hats are worn straight across the hairline or forehead. With the freedom of choice an oval faced individual has, we recommend getting one hat for everything. After all, you can never have too many hats—especially if you have the coveted oval face shape.”


Wave Bucket



Velveteen Cap



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