Essential Winter Hats for Women

There are several other styles of women’s hats that are perfect for wearing.

The weather has been nothing like it was at this time last year — hold the cheers, it’s just Jan. 4 — but it still makes good sense to dress warmly, from the top down. And staying toasty doesn’t mean sacrificing style or fashion — just ask hat lover Sharon Graham of Toledo.

“In the winter, I might wear a headband with a rhinestone. I have a mink hat that reminds you of a pill box hat,” she said, recalling the mid-20th century style that was made popular by then-First Lady Jackie Kennedy. Weather conditions — the reading on the thermometer, wind, and precipitation — often dictate the choice for the day.

“I usually put a hat on that may not cover my ears, but covers my head. To be fashionable, I usually wear a matching coat or scarf with the hat,” Ms. Graham said. She may opt for a floppy winter hat when it’s colder out. But whatever her choice, she makes a hat work in multiple ways. “My favorite is my mink hat,” she said. “I can wear it to church, the movies, basketball games. I can dress it up with a dress suit or dress it down and wear it with jeans.”

Sara Rogers, trend specialist for the Mall of America, talks about the various styles of women’s winter hats that make good practical yet stylish choices — floppy, fedora, cloche, beanie, wide brim — and how to wear them.

Floppy hat


Ms. Rogers says: Keep it easy, breezy, and bohemian with this chic 1970s vibe.

Wear it with: a faux fur vest, denim on denim, floral print dress, maxi skirt/dress, or chunky sweater and jeans and a fringe handbag.

As outerwear: Pair with biker jackets, sweater coats, shearling coats, or ponchos


Ms. Rogers says: Borrow this menswear-inspired look from the boys, but consider adding a feminine touch.

Wear it with: a T-shirt and jeans, blouse with ankle pants, tailored blazer and T-shirt, button-up shirt and a skirt or denim.

As outerwear: Pair with tailored wool coats, robe-style coats, biker jackets, and menswear-style coats.



Ms. Rogers says: This bell-shaped hat has a vintage look and gives a nod to the 1920s era. Play to its strengths with looks that hark back to the past.

Wear it with: a blazer and sweater, floral print dress, feminine blouse (tie front, Peter Pan collar, etc.), a dress and cardigan, a sheath dress, high necklines, or fit-and-flare dresses and skirts.

As outerwear: Pair with retro-inspired coats, princess coats, classic wool coats, coats with ¾-length sleeves, furry coats, or capes.


Ms. Rogers says: This head-hugging style is worn for warmth and for style. It looks edgy with core basics, and can easily take your casual look to the next level.

Wear it with: sweatshirts, sweaters layered with shirts, denim, plaid, T-shirts, or skater skirts.

As outerwear: Pair with down, wool, and leather jackets and coats; and biker and anorak jackets.

Wide brim


Ms. Rogers says: Floppy or rigid, pinched or rounded — it’s the perfect choice when you want to make a statement. It also gives the wearer an aura of mystery.

Wear it with: long skirts and a moto jacket, a sheath dress, plaid/​button-up shirts, trousers, or skirts, a blazer, T-shirt, and denim, or a fit-and-flare dress or skirt.

As outerwear: Pair with leather, wool, fur, biker jackets, capes, or ponchos.

Courtesy THE BLADE


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Women's Magazine: Essential Winter Hats for Women
Essential Winter Hats for Women
There are several other styles of women’s hats that are perfect for wearing.
Women's Magazine
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