In a world filled with off-the-shoulder tops, cropped turtlenecks, and wide-leg jeans, a beanie seems like the easiest thing to style: You put it on your head. But as evidenced by a friend who seemed truly perplexed recently—“I just don’t know where it should sit on my head or if it should flop over or stick straight up” is an actual, verbatim complaint she texted me recently—it’s not always that simple.
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You may thing you’re just not a hat person, but you’d be wrong: Literally everyone, no matter your hairstyle or head shape, can pull off a beanie. It’s just about finding the right one: while we’d never deprive anyone of the newly on-trend pom pom beanie, long faces are better off with something a bit chunkier, and round faces can pull off something tighter. To prove our point, we found 26 models, bloggers, editors, and other stylish folk wearing the winter essential, as well as a similar style to shop.
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AEO Snowflake Beanie, $20; at American Eagle


Tna Glacial Slouchy Hat, $30; at Aritzia


ASOS Oversized Boyfriend Rib Beanie, $13; at ASOS


ASOS Rib Bright Blue Faux Fur Pom Beanie, $19; at ASOS


ASOS Fluffy Super Soft Beanie, $16; at ASOS


Eugenia Kim Felix Wool Hat; $175; at Barneys New York


Acrylic Watch Hat, $10; at Carhartt


Christobelle Bow Hat, $70; at Club Monaco


Soyer Reversible Cashmere Hat, $290; at The Dreslyn


FW15 Supreme Grid Beanie Black Gray Cuffed Box Logo Classic Hat White Plaid Cap, $60; at Ebay


Ribbed Knit Beanie, $4; at Forever21


Pompom Hat, $13; at H&M


Wool-blend Hat, $10; at H&M


Pom Knit Beanie, $12; at Hollister


Cozy-Knit Beanie, $40; at Madewell


Bright Ideas Knit Beanie in Pink, $10; at Nasty Gal


Seed Bobble Beanie, $100; at Need Supply


Ribbed Beanie, $65; at Need Supply


BCBGMAXAZRIA Fiesta Beanie; $58; at Nordstrom


Hat 97023, $18; at Oak + Fort


Lightweight Beanie for Women, $5; at Old Navy


1717 Olive Cable Knit Beanie, $44; at ShopBop


Inverni Cashmere Beanie with Tonal Pom, $295; at ShopBop


Plain Fluffy Beanie, $22; at TOPSHOP


Clyde Arp Knit Hat In Acid Yellow Reflector, $88; at Garmentory


OBEY Linden Beanie, $10; at Urban Outfitters