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How to Look Cool in a Hat, According to 15 Stylish Women

Photo: Nicky Zeng

Winter dressing can feel like a game of Tetris: You carefully cover your body in layers, then frantically rearrange them depending on where you are. Step outside into the cold air? That’s one level. Find yourself in an overheated hallway? That’s another level. To extend this metaphor to the breaking point, hats are like that square Tetris piece — seemingly simple and convenient, yet surprisingly tricky to fit into many scenarios.

Below, 15 stylish women explain how they wear their favorite hats, from bucket hats to berets to beanies, so you can stay warm without sacrificing an inch of style.

Alyssa Coscarelli, Freelance Writer and Editor

Instagram:@alyssainthecity

Her hat-wearing advice:
This winter I’m usually either in a beanie or a bucket hat, my most recent favorite being this wool bucket from Gimaguas. It goes with everything, and I like that it’s a bit on the smaller side so it’s not as floppy as some bucket hats currently on the market. It stays on my head despite any winter gusts of wind.

Pringui Hat
Chloe Canvas Bucket Hat

Mi-Anne Chan, Video Producer, Writer, & Host at Refinery29

Instagram: @mianne.chan

Her hat-wearing advice:
Hats are a bit like 2 a.m. bodega sandwiches — hit or miss. But speaking of bodegas, I’ve found a handful of cheap-ass beanies and snapbacks at random delis, thrift stores, and souvenir shops over the years. I found the bucket hat in this photo at an extremely touristy shop in Singapore’s Chinatown, right next to the magnets and postcards. It cost me all of $8 and it’s reversible! I’m still on the hunt for more bucket hats, though. I’m eyeing this neon orange number from Dick’s Sporting Goods.

Field & Stream Men’s Blaze Jones Hat
Holly Pavement-Print Satin Bucket Hat

Jennifer Abey, Fashion Consultant and Marketing Student

Instagram: @jennabey

Her hat-wearing advice:
Bucket hats are my favorite. They’re simple to style and you can easily match them with every outfit, since they come in every color, pattern, form, and textile. The last one I bought was a light blue one in a PVC material from Burberry, but the most classic brand for bucket hats is definitely Kangol. They have a large range of color and they’re really warm.

Manokhi Vinyl Bucket Hat
Kangol Bermuda Bucket Hat

Minne Atairu, Artist and UX Designer

Instagram: @usominne

Her hat-wearing advice:
Bucket hats were always on a list of “Things I Would Never Try” until I came across a patent-leather version at Nordstrom. I often wear mine with matching orange sunglasses and an oversize blazer — a combo which I believe adds the right dose of interesting to my overly utilitarian winter look.

Driptidoo Patent Bucket Rain Hat
Leopard Bucket Hat

Erica Kim, Architectural History and Urban Design Professor

Instagram: @ahistoryofarchitecture

Her hat-wearing advice:
I found my favorite beret for $30 in a local Toronto shop. I always try them on because the fit can vary a lot. When I shop for berets, I look for bright colors and a smooth close fit similar to Faye Dunaway in Bonnie and Clyde.

Felt-Wool Beret
Samuji Brown Beret Hat

Ella Sisso, Influencer

Instagram: @fatgirlinspo

Her hat-wearing advice:
I’ve recently got into newsboy hats which I like to wear with long wavy wigs for a ’70s feel, but my favorite hat is a beret. I’ve got about six in different colors and I’ll wear them with any outfit and any occasion. They are so versatile and I love the way they can add color to any look. I find mine on eBay and at market stalls.

Felted Wool Beret

Ryan Norville, Florist and Content Creator

Instagram: @cinnamonryan

Her hat-wearing avice:
A bucket hat or baseball cap looks better with a slouchy or menswear look, while a beret or newsboy cap is best with a more tailored or dressy outfit. I wore a beret here as I thought the black wool complemented the maximalist textures of the rest of my outfit — plus, how could I go to Paris and not wear a beret?

Hat Attack Wool Beret Hat
Photo: 18-09-10 eloiseopryszko AM2 B4 davidaustin W
Hat Attack Wool Beret Hat
Holly Floral Bucket Hat

Kelly Augustine, Influencer and Marketer

Instagram: @kellyaugustineb

Her hat-wearing advice:
I’m a serious beret lover because they come in so many textures and styles, so it’s easy to mix it up. I have lots from Zara and Topshop and love this embellished one from Frances Grey. I like to style them with a bold lip color and statement earrings.

Rebecca Ramsdale, Content Creator

Instagram: @rebeccaramsdale

Her hat-wearing advice:
My favorite hats are usually a bit over the top. I love anything bright and out of the ordinary — which typically end up being vintage or thrifted. My most recent hat purchase was from the brand Lloyd, and is a short fluffy beanie made from a vintage cardigan. Mine is pink and very cute.

Farrow Xenia Fuzzy Acrylic Beanie
COLLUSION Unisex Fisherman Rib Beanie

Maren Schia, Influencer

Instagram: @marenschia

Her hat-wearing advice:
I love the hat in the picture — it’s from the Norwegian brand Cala Jade. My styling tip is to match your hat to another item in your outfit, so it looks more put-together. Next on my wish list: The Prada Knitted Bucket Hat, because I really like the idea of that fabric for a bucket hat and it seems more appropriate to use in the Norwegian cold weather.

Prada Zigzag Logo Bucket Hat
Brixton Churchill Faux Fur Cap

Jennifer Barthole, Senior Fashion Editor at Shape

Instagram: @jennbarthole

Her hat-wearing advice:
A beige beanie is a staple in my winter wardrobe because it compliments everything from my sporty puffers to more elevated (faux) fur coats. Uniqlo’s Heat Tech Knitted Cap is my absolute favorite for everyday wear because its insulated fabric keeps me toasty, but it’s also moisture-wicking for the inevitable sweaty subway ride.

HEATTECH Knitted Cap
Pansy N Face Hat
Photo: 18-12-28 melissamartinez PM2 B3 johnficenec W
Pansy N Face Hat

Kellie Brown, Blogger at And I Get Dressed

Instagram: @itsmekellieb

Her hat-wearing advice:
Pay attention to texture. I’ve learned that a chunky beanie works so much better on me than a thin-weave beanie because it looks more relaxed and effortless. Plus my hair fits more naturally and I’m not dying to snatch it off the second I’m inside.

Cashmere Beanie
Majestic Filatures

Laura Jung, Food and Travel Influencer

Instagram: @laurajung

Her hat-wearing advice:
I see hats as functional as well as cute — which means they need to be warm. Berets, beanies and Lenin hats are my go-to. My style is pretty casual and very weather-dependent so I’ll base my hat choice around that. I buy most of my hats when I’m home in Seoul, Korea. I feel like they know how to make hats that fit Asian faces really well. Brixton is super affordable and has something for everyone. But I swoon over Eugenia Kim, Lola Hats, and Maison Michel.

Chain Wool Blend Baker Boy Cap

Melissa Adames, Content Creator and International Law Admin Assistant

Instagram: @lulamelissa

Her hat-wearing advice:
For winter hats, I look for a soft and cozy textures and neutral colors. I also tend to stick to classic styles, so that if I need to throw a hat on randomly I won’t have to worry about it clashing with my outfit and outerwear. I think Topshop, H&M, and & Other Stories always has a great selection.

Mattie Fisherman Cap
Ashland Corduroy Newsboy Hat
Photo: 18-08-29 anjacihoric PM1 B6 ryankautzer W
Ashland Corduroy Newsboy Hat

Tyla-Lauren Gilmore, Influencer

Instagram: @tylauren

Her hat-wearing advice:
I wear hats all year around — they’re my favorite accessory. I usually get them from H&M, Forever 21, or Primark. As of late, I’m obsessed with wide-brim hats, beanies, and newsboy hats. I would pair a baker boy hat with a monochromatic turtleneck-and-trousers look.

Corduroy Cabby Hat

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How to Look Cool in a Hat, According to 15 Stylish Women