“Is this cute? Or do I just look silly?”
How many of us have asked a variation of that when trying on hats? Who has a small pile of newsboys, berets and fedoras sitting unworn on a shelf somewhere? For some reason, hats have a tendency to leave even the most fashionably confident questioning their choices.
It’s no secret: Hats can be tricky. Hairdos, face shapes and personal styles all affect how we look in hats, and what’s darling on one head can look daffy on another.
Before dismissing all headwear, though, take a look at our guide to this winter’s styles. In general, try a hat that balances your face shape. If you have round or square features, go for hats with higher crowns and small to medium brims to add length; long faces should opt for lower crowns and wide brims. Similarly, those with angular features should try rounded styles and vice versa.
And remember, whether a hat looks good on you often comes down to confidence. Hats are powerful and striking—wear them like you mean it.
Perfect for: Everyone
Perhaps the most versatile hat, berets look good with almost every hairstyle and face shape, and come in a nearly unlimited variety of colors, patterns and fabrics. We like them in solid colors but with interesting textures, like the chunky knit seen here. Pull it down low on your forehead and tuck in your hair, or sit it back on the crown of your head and let your bangs sweep out for a more laid-back look.
Tarnish Seed Stitch Beret, $42, Nordstrom
Perfect for: Cheeky Ladies
This season’s ladylike gals should take a cue from 1920s flappers, who popularized this sweet but cosmopolitan style. The cloche also works with a variety of hairstyles, whether you’ve got a close crop, long curls, or a low bun. Wear with sleek wool or trench coats and leather gloves.
Hat with Side Bow, $29.90, Zara
Perfect for: Drama Queens
These hats may look overly theatrical, but they strike the right balance when paired with simple peacoats or one of this season’s streamlined military styles. The earflaps can be tied up or left loose depending on the temperature, making for an extremely functional hat, while faux fur adds a layer of luxe for the most dramatic of winter statements.
Aqua Quilted Rabbit Fur Aviator Hat, $75, Bloomingdales
Perfect for: Hip 20- and 60-Somethings
Truth: The fedora may be the hardest hat to pull off, and typically works best for younger or older women with sly senses of style. For your first fedora, keep it simple with a neutral color and modest brim. This hat looks best with hair worn long and wavy
Bop Basics Floppy Fedora, $78, Shopbop
Perfect for: Ski Bunnies
A knit trapper with earflaps and pompoms is ideal for battling wind and snow, whether you’re on the mountain or Michigan Avenue. This style is for sportier types and works well with puffers and duffle coats. Those with long hair should wear it loose or braided.
Grey Fairisle Patterned PomPom Knitted Trapper Hat, $32, Topshop
Perfect for: Anyone Afraid of Hat Head
Fortunately, those of us who’ve adopted hair’s trendy topknots can still keep our ears warm. This season you can find several styles in faux fur, but we also love adding a touch of plaid to our winter wear. Classic.
Burberry Giant Check Earmuffs, $175, Saks Fifth Avenue