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The Five Best Winter Hats For Women 2019

Wide brim rancher hat winter outfit, holiday style, hats under $100, fashion blog, wardrobe stylist

HAT (just $44) // SWEATER // SCARF // COAT (similar) // JEANS (similar) // BAG

Wintertime is the best time for hats because there are so many styles to choose from to warm you up, fit your facial shape, and suit your style. A wide brim rancher? Boho chic. Beret? Femme sophistication. Knit beanie? Casual cozy!

A cute winter hat is like a two-fer for winter fashion. You get a nice style boost and keep your noggin' warm to boot. We lose a lot of heat through our heads so keeping them covered in cold weather is key! But. I can already hear many of you saying "I don't look good in hats." I don't believe that, for starters, but it could be true you haven't found the right hat for you! Let's fix that.

These are the five best winter hats for women to wear while baby it's cold outside.



Wide brim rancher hat winter outfit, holiday style, hats under $100, fashion blog, wardrobe stylist

A rancher, a panama, a fedora...they all fall into the wide brim hat category. The difference is in the width of the brim, and the stiffness of it. A rancher has a wider, very stiff brim. A panama hat's brim is shorter and sometimes stiff, sometimes more malleable. The brim makes these hats liable to fly off on blustery days so dress accordingly (or keep one hand free to catch your topper before it sails into the trees)!

Sole Society Wide Brim Hat w/ Leather Band, $35. Real wool hat with a wide leather band around the base that creates color contrast. Comes in six colors.

UO Felt Brim Rancher Hat, $44. Looks just like Lack of Color, but a 1/3 of the price. Comes in six colors including black, brown, and neutral taupe.

UO Felt Panama Hat, $39. Shorter, flexible brim. Smaller overall shape than a rancher. Comes in six colors including black, olive, tan, and a snakeskin leather trim.

Blanche Rancher, $68. The rare find of a white, navy, or red rancher hat for under $100.

Lack of Color Celestial Boater, $199. The big brand behind wide brim hats. Pricier when you can find inexpensive lookalikes, except for certain styles like this dreamy boho embellished boater.



Chunky knit pom beanie, Target, holiday style, hats under $50, fashion blog, wardrobe stylist

The poster child of winter hats. Cold days, snow days, windy days, ski days...they're often fashionable and always functional. I prefer a knit beanie with a pom to prevent the "egg head" look but that's my personal preference. A chunky knit will look softer while a thinner one will appear more sleek on the head.

Target Wild Fable Chunky Knit Beanie, $12. A oversized thick knit beanie with pom detail from our favorite store. Comes in five colors.

Old Navy Fair Isle Beanie, $7 (prices vary depending on sale). You can't beat Old Navy's holiday sales, or their yearly festive Fair Isle winter accessories. This year's print comes in black and white, and multicolor styles. Grab the matching scarf to complete the set.

Abercrombie Chunky Knit Beanie, $34. Chunky without looking huge on your head. Always get compliments on this one!

Remember...beanies can be dressed up, too! Wearing this $15 Target beanie.

Chunky knit pom beanie, Target, dressy holiday style, hats under $50, fashion blog, wardrobe stylist



We're all thinking French girl style right now so let's just acknowledge it. I love a beret in the wintertime as a chic alternative to the knit beanie. If you're traveling to a cosmopolitan city, or dressing up for a cold date night evening out, consider the beret. Easy to pack, stays on your head.

Halogen Wool Blend Beret, $29. Comes in all the classic neutrals plus fun colors like cobalt blue and red.

Banana Republic Pearl Beret, $48. Small pearl clusters on a winter white wool beret? Tres chic!

Also consider the cloche hat for more head coverage while maintaining the dressier look. These fuzzy cloche hats with floral detail are under $20 and super cute!

Wool beret, chic holiday style, hats under $50, fashion blog, wardrobe stylist


There's some confusion over the proper name of this hat. Newsboy cap, baker boy hat, engineer's cap...all I know is various men out on the grind wore some variation of this hat back in the day. We have another 'pay attention to the construction' advisement here. Some styles are poufy on top while others are more rigid across the front. It's a stronger look than a beret or wide brim hat but it's tons of fun with the right 'fit!

Wearing the Lola Cap from Nest Boutique -- get 15% off your purchase with code BROOKE15. Also check out their vintage sailor cap by Lack of Color!

Newsboy hat, engineer cap for women, baker boy hat, Target, holiday style, hats under $100, fashion blog, wardrobe stylist


The winter hat for the chic survivalist inside of us all. Wear with your parka coat and leggings, or ham it up indoors with your trapper hat and Christmas pajamas. I wore mine for our Christmas card pics last year!

Sherpa Trapper Hat, $49. Faux suede with sherpa trim and a pom detail.

Faux Fur Trapper Hat, $50. Faux fur all over the outside including on the ear flaps. Also comes in buffalo plaid! (Compare to Target's version for $17.)

Snow Castle Trapper Pom Hat, $68. Marbled knit with faux fur poms on the top and ear flaps.

Trapper hat for women, holiday style, hats under $100, fashion blog, wardrobe stylist

Do you like to wear hats all winter long? Which style is your favorite? They're such a fab solution to a bad hair day that I rely on A LOT! It's amazing how hiding a hot hair mess with a hat can result in elevating your overall outfit.

Thank you for coming by the blog today! I so appreciate your time and support!


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