The Best Hats for Your Face Shape

Hats are kind of like sunglasses – you’d kill to pull off aviators, but they look, well, awkward without the right face shape. And like sunglasses, hats are an accessory staple and every collegiette ought to find her fit. That’s why we consulted with fashion stylist, Gayle Zerafa Cutajar to give us the lowdown. “I call them head jewelry and they aren’t just for cold weather or bad hair days anymore,” she says. “You can upgrade your look by rocking the right hat, taking into consideration the structure of your face.” We’ve broken it down to our five favorite hats for fall that work for square, oval, round, oblong and heart face shapes.

Square Faces: Bowlers

Celeb examples: Sandra Bullock, Angelina Jolie

According to Cutajar, collegiettes with square faces should wear hats that soften their rigid angles. “Floppy, curvy hats accomplish this task, giving them a feminine and flirty touch,” she says. These are hats with large or upturned rims – like felt material floppy hats. But if you’re not down to wear something that attention-grabbing, go for hats that will elongate your face. Cutajar suggests hats that sit high on your forehead, like bowlers.

Eugenia Kim Genie,, $77
Felt Roll Brim Bowler,, $35
Mini Felt Bowler Hat, Urban Outfitters, $29
Mini Roller Hat,, $50
City Bowler,, $78
Dome Hemming Blue Bowler,, $22

Oval Faces: Berets

Celeb examples: Kate Hudson, Sarah Jessica Parker

Lucky for oval-shaped faces, you can pull off just about any style hat. “Therefore, go with whatever suits your mood—fedoras, cloches, newsboys, beanies, anything,” says Gayle. With that many to choose from, how can you narrow it down when shopping? We suggest berets for this fall in wool, knit, ribbed or even topped with a pom.

Cocoon Beret Hat, Urban Outfitters, $24
Parkhurst ‘Basic’ Wool Beret, Nordstrom, $24
Unisex Wool Beret, American Apparel, $24
San Diego Hat Co. Pom Beret,, $34
Nordstrom Collection Ribbed Cashmere Beret, Nordstrom, $58
Helen Kaminski Jocelyn Wool Beret,, $134