8 ways to wear a winter hat and still look cute (yup, it’s possible)

It’s pretty obvious that shielding your head with a warm hat is crucial in crazy-cold weather. But like any item of clothing that is more practical than fashionable, pulling it off in a chic way isn’t exactly easy.

We’ve previously rallied up a few street style-approved advice and hats for you, but for some closer-to-home inspo, how about advice via Canadian gals who know what it’s like to deal with freezing cold temps? This week, we challenged Style Panel and asked them to share their tips for rocking a hat this winter. From choosing the right colour and style to pairing it with certain pieces, here are eight ways to wear your winter hat this winter without looking crazy.

Question 153: How do you wear your winter hat? Read the answers now! »


how to wear a winter hat carleton

Carleton Eckhardt, 30
Toronto | Carleton Eckhardt

Staying warm and fashionable in the winter can be a little difficult at times. Luckily, there are so many amazing winter accessories that pair fashion with function for our cool northern climate. I simply can’t live without one essential in particular and that’s the perfect winter hat. A simple, slouchy toque in super soft cashmere is my personal preference. I prefer neutral colours such as black, grey or cream because they pair well with just about any outfit and add a chic touch in the chilliest weather.

Carleton’s wearing: Hat, Wish List YYZ. Coat, Gap. Jeans and sweater, M for Mendocino. Shoes, Zara.


how to wear a winter hat teresa

Teresa Yoo, 25
Toronto | What T Loves

A good hat is a crucial winter shopping investment, especially if you live in Toronto. Hats are extremely useful during the colder months, but kind of hard to pull off in a fashionable and chic way. Therefore, each year I go on a major hunt for a very few, specific hats that I don’t feel silly in, but still practical enough to save myself from freezing. I have only two things in mind when I go hat shopping. One, go for the easy colours like black, grey or anything neutral. Two: look for cute but subtle details for the fashion portion. The result? This wool and cashmere hat with beading designs all over.

Teresa’s wearing: Hat, Club Monaco. Turtleneck, Zara. Shirt, Thrifted. Skirt, Club Monaco.


how to wear a winter hat barbara
Photography by Trevor Negin

Barbara Ann Solomon, 28
Toronto | Barbara Ann’s Style Blog

This year my favourite outdoor accessories have all sorts of personality, like this bear hat that I’ve fallen in love with. I’ve paired it with everything from my super-warm parka to my leather biker jacket and I find it always brings a smile as people see it dressed-up all chic.

Barbara’s wearing: Sweater, Halogen Cashmere. Hat, Urban Outfitters. Glasses, Clearly.ca.


how to wear a winter hat shauna

Shauna Dean, 27
Windsor | Quentin & Co

I love using my winter hat to add an unexpected twist to my look, especially for workwear! It never fails to give an edge to my go-to office uniform of a pencil skirt and turtleneck. My morning commute is so much warmer and chicer once I add a hat, and this winter white toque paired with a lace skirt is the perfect combination of feminine polish and laid-back cool.

Shauna’s wearing: Hat, H&M. Turtleneck, H&M. Pencil Skirt, Kora Rae.


how to wear a winter hat laura

Laura Mitbrodt, 31
Victoria | Laura Jane Atelier

I feel lucky that I don’t have to deal with crazy winter weather like the rest of Canada. Everything has started to bloom here in Victoria, but it can still get chilly, especially at night. I like to wear my cute Love Kiwi Hat with the baby blue pompom on top on those cold nights. I find that the pompom adds a cute, playful detail and the cream colour is a breath of fresh air on a cold winter day.

Laura’s wearing: Hat, Love Kiwi. Coat, Chic Wish. Top, Design Lab. Jeans, Design Lab. Necklace, Charming Charlie.


how to wear a winter hat kayla

Kayla Short, 29
Halifax | Short Presents

We will undoubtedly have the best hair days when we need to toss a hat on top of it. Such is the way of winter. Luckily there are some super cute options to keep you excited about winter accessories. While most of us would rather choose a great hair day over an adorable hat, this oversized pom pom hat definitely helps ease the blow.

Kayla’s wearing: Hat, Envy Clothing. Jacket, Old Navy. Scarf, Fraanklin. Boots, Rockport. Jeans, Gap. Mittens, Le Château. Sunglasses, Céline via Smart Buy Glasses.


how to wear a winter hat stephanie

Stephanie Koch, 30
Kelowna | Inherited Jeans

The good news about sporting winter gear in Canada is that we are all in this together. Everyone needs to wear something warm to get by this season, and it’s tough to look entirely glamorous in it. My solution to wearing hats without looking fully ridiculous in the winter is to wear one that goes with what I have on underneath my coat and not really take it off. I prefer beanies to fedoras when it’s really cold out because they can cover your ears and won’t be caught by the wind. Look for ones with details like a chunky knit or a pompom to make it a bit more fun, and feel good that you are the lady that is keeping warm (and that no one can see your frizzy hair)!

Stephanie’s wearing: Hat, Wilfred Free by Aritzia. Shirt, Babaton by Aritzia. Scarf, Joe Fresh. Jeans, Anine Bing. Boots, Sam Edelman. Coat, Pink Martini.


how to wear a winter hat meagan

Meagan Faye, 26
Vancouver | Living Boldly

When it comes to winter hats, I always turn to felt to keep my head cozy and stylish. Unlike other materials, felt won’t freeze and it’s great for protecting your hair from the rain or snow.

I love adding a wide-brimmed hat to a layered winter look. It adds an element of style that prevents you from looking (and feeling) like the Michelin Man and can help you look dressed up even in your coldest moments.

Meaghan’s wearing: Hat, Forever 21. Sweater, H&M. Coat and pants, Chicwish. Boots, Zara.