Style Guide: How to Pick the Best Winter Hats for Women

Admit it, ladies. When temperatures drop and the cold weather sets in, that's when your style quotient heats up with loads of layering and carefully curated accessories. Just like a cozy scarf, cashmere sweater, and statement coat are winter wardrobe essentials, a fabulous winter hat is a must.

Fortunately, there are plenty of fashionable options for any situation or setting. Find out what to look for in a winter hat, plus shop the hottest looks so that even when the weather is drab, you'll always look fab.

Winter Hat Tips

Choosing the best winter hat is more than just finding one that fits. Follow these few easy steps to successfully pull off your winter headwear.

Find Fabric With Flair

You deserve some credit for dealing with such harsh weather. Look for hats in luxe fabrics such as cashmere or fine merino wool. Pay attention to mixed textures such as sheepskin or faux fur lining for added glamour and warmth.

Play With Proportion

When it comes to picking a winter hat, don't be afraid to try something new on for size. But that doesn't mean wearing the wrong size — consult our hat sizing guide to make sure you have the perfect fit. If you usually wear a close-fitting cuff beanie covering your ears, try a slouchy beanie worn above your ears. Or if you tend to favor short-brim hats, give a wide-brim topper a chance. Remember, it's just a hat, not a tattoo.

Get Creative With Color

If you typically opt for basic black or other neutral tones, consider pushing your palette to try new things. Perhaps wear a bright orange pom-pom hat to add a pop of color to an otherwise monochromatic look.

Womens Winter Hat Styles

The weather outside is frightful, but these stylish winter hats are so delightful. Shop these top picks then peruse our wide selection of womens wool hats.

Winter Beanie

Style Guide: How to Pick the Best Winter Hats for Women - Beanie

Probably the most popular winter hat style that comes in virtually every shape, color, and fabric, a beanie is an absolute must in every woman's winter hat wardrobe. Universally flattering for petite to large frames and versatile enough for multiple occasions, beanies can be as serious or playful as you want.

For a fun take on this warm hat must-have, try a ribbed pom-pom beanie with your favorite cowl neck sweater. For a touch of luxury, treat yourself to warm beanie in cashmere or merino wool. Or try a chunky knit beanie to take advantage of the excellent insulation it provides.


Much like beanies, berets are soft, brimless hats that are flattering on all women. Often made of wool, crocheted cotton, or acrylic, berets make a good winter hat for the most part. However, unlike beanies, they don't cover the ears. That's why it's a good idea to compensate with a chunky knit scarf or faux fur collar to keep yourself warm.

There really is no wrong way to wear this iconic French chapeau, so try different angles — tilt it to one side, center it on your head, or experiment wearing it backwards. Finish off a stretch cable-knit sweater, plaid skirt, tweed coat, and black leggings for a fun day-to-night look that will work at the office or out with friends. Our recommendation: Pittsburgh by Scala. This true basque beret is made in France, making it as "authentique" as they come.

Wool Fedora

For winter weather accessorizing, you can't go wrong with a classic wool felt fedora. (If you've heard otherwise, that's all the fault of the trilby hat. Take a look at our guide detailing the difference between a fedora vs. trilby and you'll know what's up.) With its soft brim, center crease, and signature pinches on each side, a fedora will instantly zhoosh up any outfit.

Combine a floppy fedora with a pair of leggings, oversized sweater, and cozy winter boots for a stylish daytime look. Or pair a wide-brim fedora with a plush coat, dress, and knee-high boots for a glammed up night on the town.

Aviator Hat

There's nothing like an aviator hat to say winter has arrived. Also known as a trapper hat or an ushanka ("ear flap hat" in Russian), an aviator hat is noted for its two ear flaps that can either be left hanging or folded back and tied up.

Although these cold-weather hats are often made from real animal fur, there's no reason not to go cruelty-free with a faux fur version, like the Florent by Scala, that will keep you just as warm and toasty.

Sure, an aviator hat can be an acquired taste (especially when worn with the ear flaps down), but they are phenomenal head warmers. Tie back the ear flaps for a more streamlined look and pair it with a faux mink jacket, ribbed turtleneck, and dark-wash denim.

Ball Cap

Surprised to see a baseball hat make the list? Yeah, thought you might be. But wearing this ultra-casual classic can actually be quite chic if you choose the right fabric, color, and style.

Whether it's a snapback, strapback, or fitted ball cap, look for cold-weather fabrications such as cashmere, wool blends, or crushed velvet to keep your head warm. Consider rich jewel tones — wine, emerald, indigo, aubergine — to give your entire ensemble a sense of laidback luxe. Or simply wear your ball cap with a puffer jacket from Patagonia or The North Face for a fuss-free day in the snow.

Winter Fab

When fighting the cold weather without sacrificing your fashion sense is a must, a winter hat is just what you need. With so many options ranging from anything-but-basic beanies to fabulous fedoras and other winter-approved headwear, the key is knowing what best suits the situation and your personality.

Whatever you decide, womens winter hats have plenty to offer when it comes to style and substance. Be sure to shop our full selection of womens wool hats and felt hats and you’ll be ready to fight the chill in style.

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Style Guide: How to Pick the Best Winter Hats for Women

Find out what to look for in a winter hat, plus shop the hottest looks so that even when the weather is drab, you'll always look fab.