The classic fedora gets an update with a wild cheetah print. Xhilaration, $13; Target.com
A ladylike cloche —à la Coco Chanel—is a sophisticated choice for workdays. San Diego Hat Company, $54; SanDiegoHat.com
Metallic threads and a patent buckle dress up a casual tweed bucket hat. Merona, $17; Target.com
Ribbon and rhinestone trim on this structured felt hat suggests a vintage find.
Hats by Selima, $338, Henri Bendel; 800-423-6335
The beret is back this fall; this slouchy knit version earns its stripes. $9.50; OldNavy.com
A cable-knit, cotton-wool hat with a brim is the winter version of your favorite baseball cap. $27; LandsEnd.com
Elevate your everyday peacoat by pairing it with this silver Lurex fisherman's cap. $30; JCrew.com
Black sequins glitz up a winter-white beret.
Liz Claiborne New York, $44; 800-555-9838 for stores
Channel Mary Richards with a chunky popcorn-stitched tam. $30; Aerie.com
The perfect ski cap: quick-drying, handknit acrylic with a fleece lining and homespun Nordic pattern. $40; Nobis.ca
Fit to be tied—or not. The ribbons on this fun faux-fur hat look great either way. $75; HatAttack.com
This water-resistant trapper, insulated with Primaloft and lined in faux fur, can handle the coldest temperatures. $40; LLBean.com More Great Looks for Winter