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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, shopbop.com, $77
Felt Roll Brim Bowler, ASOS.com, $35
Mini Felt Bowler Hat, Urban Outfitters, $29
Mini Roller Hat, topshop.com, $50
City Bowler, jigsaw-online.com, $78
Dome Hemming Blue Bowler, romwe.com, $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, Lulus.com, $34
Nordstrom Collection Ribbed Cashmere Beret, Nordstrom, $58
Helen Kaminski Jocelyn Wool Beret, Saksfifthavenue.com, $134

Round Faces: Newsboy Caps

Celeb example: Kelly Clarkson

“Round faces are cute, but they often look short and full,” says Cutajar. “To offset these characteristics, go with hats that are tall and shallow, which will give your face length.” She suggests slanted or peaked crowns–think newsboy caps, where you can slant the hat forward to give your face more angles. Try choosing ones where the front brim is slightly wider than your face shape.

Halogen Tweed Tuck Newsboy, Nordstrom, $30
Echo Marled Stitch Newsboy, Nordstrom, $35
Echo Marled Stitch Newsboy, Nordstrom, $35
Women Jockey Cap, uniqlo.com, $24
Wool Cap, dkny.com, $55
Flat Cap, hm.com, $13

Oblong Faces: Turbans

Celeb example: Kelly Rowland

Oblong faces are long, which means you should “avoid tall hats like a stage-five clinger,” Cutajar jokes. “They only make your face look longer.” Mad-hatter toppers that popped up on this fall’s runways won’t do. She suggests hats that are flared or have wide brims. You can get away with this season’s crop of bowlers or floppy hats, but in the spirit of style, why not try something that’s in this season? Turban hats are intimidating at first, so try them in knits or headbands. Turbans, along with wide brimmed hats, can also be pulled down on your forehead to make your face seem shorter according to Cutajar.

Coal The Paige Turban, revolveclothing.com, $22
Grace Hats Tokyo, karmaloop.com, $42
Grace Hats Tokyo, karmaloop.com, $36
Alice Hannah Twisted Rib Turban, asos.com, $37
Chunky Knit Turban, ASOS.com, $17
Little Fille Laetitia. Botica.com, $44

Heart-Shaped Faces: Beanies

Celeb example: Christina Ricci, Jennifer Lopez

Like ovals, collegiettes with heart face shapes can get away with pulling off just about any hat. The catch is to avoid the hat accentuating your forehead. “Ladies with heart-shaped faces have wide foreheads and narrow chins,” Cutajar says. “Because of this contrast you should avoid wearing wide hats,” like floppy or sun hats. For fall, your best bet is beanies that come in comfy knits and are always easy to find.

ASOS Metallic Silver Boyfriend Beanie, ASOS.com, $14
ASOS Faux Fur Pom Boyfriend Beanie, ASOS.com, $17
Two Tone Zigzag Beanie, Topshop.com, $24
Agent Ninetynine Ellen Beanie, Generalpants.com, $31
Wooden Ships Open Knit Beanie, Freepeople.com, $38
The North Face Hat, Macys.com, $38

If you’re iffy about your face shape, consult our celeb examples above. Because once you know which hats makes you look your best, you’ll never waste them on a bad hair day again.


Tricia is a senior (2012) at Central Michigan University, studying English Literature and French. She was the Campus Life editor at her school's feature publication, Grand Central Magazine, interned at BlackBook Magazine, and spent a semester in France, followed by some time in India. She's all about women's interests and issues. Follow Tricia on Twitter @TriciaTaormina.
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