Hate wearing a winter hat? 11 Style Panel tips to making your beanie, toque, fedora and headband work (minus the hat head)

Winter Hat

It’s hat season, though many would like to avoid it. For some of us, the idea of wearing a hat may induce horrific memories of flat, static lifeless hair, and unfortunate style choices we may have made when we were young (we’re looking at you, Doctor Seuss hat). Let’s face it though, winter hats are hard to avoid, and actually quite essential to staying warm all season long.

Beanies and toques were the style of choice for many of our Style Panel members, and there is no question why. Beanies provide ultimate ear warmth while remaining the simplest style to wear on a particularly bad hair day. But if getting hat head is a concern, earmuffs and headbands do just the same trick while leaving your hair relatively untouched. For a more fashion-forward take on the look, trying a Russian-style faux fur headband like Barbara Solomon’s adds an extra touch of luxe.

Question 28: What is your go to hat or head covering for winter and why is it your favourite? Read the answers now! »

Or jump to: ALEXANDRA NIKOLAJEV, TORONTO | ALICIA QUAN, VANCOUVER | ALYSSA LAU, EDMONTON | BARBARA ANN SOLOMON, TORONTO | JEN TAM, VANCOUVER | KASSANDRA CAMPONI, EDMONTON | KAYLA SHORT, HALIFAX | KRISTIN MACDONALD, FREDRICTON | MO HANDAHU, HALIFAX | VICKIE LALIOTIS, EDMONTON | WHITNEY COSGRAVE, LOS ANGELES

Winter Hat: Alyssa Lau, Ordinary Peoples

Alyssa Lau, 20
Edmonton | The Ordinary Peoples

Hat season (more so beanie season for me) has always been my favourite because all it really means is that I no longer have to spend time on my hair. In other words, I can sleep in for an extra fifteen minutes in the morning. Another plus is that my ears will stay toasty while the rest of me freezes.

Alyssa’s wearing: T shirt, Oak + Fort. Blouse, Nordstrom. Boots, Boutique 9. Beanie, ASOS. Bag, Choies.

Winter Hat: Vickie Laliotis, Adventures in Fashion

Vickie Laliotis, 28
Edmonton | Adventures in Fashion

When it comes to warming up on a cold winter’s day, beanies are by far my favourite cold-weather accessory. Not only do they keep me toasty warm, but they also do wonders on bad hair days. There’s no limit to the styles and colours at my disposal, so I see no reason not to stock up with as many beanies as possible this winter!

Vickie’s wearing: Sweater, Forever, 21. Dress, Forever 21. Faux Fur Cowl, Michael Kors. Tights, Joe Fresh. Boots, Forever 21. Beanie, H&M. Bracelets, House of Harlow and The Bay. Watch, Michael Kors.

Winter Hat: Jen Tam, Her Waise Choice

Jen Tam, 23
Vancouver | Her Waise Choice

My head covering of choice for the winter months is a wool brimmed hat. It not only keeps me warm, but works well with my face shape by balancing out my fuller cheeks! I also love the city-chic look it provides to the most casual of outfits.

Jen’s wearing: Sweater, JNBY. Snood, YesStyle. Skirt, Zara. Hat, Board of Trade Co. Heels, Joe Fresh. Bag, Vince Camuto.

Winter Hat: Alexandra Nikolajev, I'm a Little

Alex Nikolajev, 27
Toronto | I’m a Little

How do I say this without sounding like a crazy person? Hats are my jam. Perhaps it’s my oversized head or the unruly, hippie hair I tend to rock for weeks on end but any way it’s sliced, I love a good hat day. And what a better time for hats? It’s cold and I definitely don’t want to wash my hair 24/7, only to have it freeze in the chill of the morning commute to the subway. While I have a variety of head accessories for every occasion (think: headbands for the slopes and berets for work attire) this Hello Kitty one has to be my favourite piece to pull out of the ol’ tickle trunk (I may or may not have named my dog after said hat’s character). Simply paired with a cream leather jacket (not shown), I always love using it to add a little playfulness to a plain outfit. It is the perfect winter accessory for a casual look and one that lends a bit of fun & fervour to a laid-back winter night out!

Winter Hat: Mo Handahu, Curvy Geekery

Mo Handahu, 29
Halifax | Curvy Geekery

When it comes to head gear for the winter I am all for any random fabric I find with an amazing print that I can wind up into a turban. It’s the best way for me to not only protect my hair but to also stay true to my style.  I love wearing turbans because with infinite printed fabric and ways of tying turbans each day can have its own unique turban.

Mo’s wearing: Dress, coat and jewellery, thrifted. Shoes, Urban Outfitters.

Winter Hat: Barbara Ann Solomon

Barbara Ann Solomon, 25
Toronto | Barbara Ann’s Style Blog

If I learned one thing from a crazy commute back and forth from Markham to OCAD University through my 4 years there, it was to always come prepared during the winter. I usually have either a silly or bright beanie stuffed in my purse. That was until I found this amazing headband last season. To me this is a game changer. The Russian and vintage inspired headband does a great job in keeping my head warm, without destroying my hair. Faux fur also adds amazing texture while framing the face.

Barbara’s wearing: Dress, H&M. Headband, American Eagle. Scarf, Roots. Heels, Pegabo. Watch, Michael Kors. Necklace, Grandmother’s. Bracelets, Club Monaco.

Winter Hat: Kayla Short, Short Presents

Kayla Short, 26
Halifax | Short Presents

Here in Halifax the temperatures tend to drop quite significantly, but that doesn’t mean I stop going outside. I live very close to the Halifax oval, and so in order to go skating outdoors I need to bundle up quite heavily. For winter I really embrace knitwear to keep me warm; I love hats, scarves, and especially headbands. My mother has many talents, and knitting is certainly one of them. With a plethora of choices I still come back to headbands time and time again because you can wear them with your hair down with some straight or curly locks, or with you hair pulled back in a sleek ponytail. It’s a win-win: stylish and practical. Love it.

Kayla’s wearing: Skirt, Tommy Hilfiger. Jacket, H&M. Boots, Very Volatile. Tights, Calvin Klein. Bag, Christopher Kon. Scarf, Burberry. Gloves, Ralph Lauren. Headband, handmade by Kayla’s mother.

Winter Hat: Whitney Cosgrave, See Shop Eat Do

Whitney Cosgrave, 25
Los Angeles via Vancouver | See Shop Eat Do

I have never been much of a dressy hat person, but when I spied this one in a department store in Paris I knew I had to have it! This floppy wool hat is my new go to for when it’s raining, and it’s also perfect for covering up a bad hair day. I also absolutely love to wear cozy beanies and will definitely be wearing them when I go home to Canada for Christmas…they don’t really work here in LA!

Whitney’s wearing: Jeans, Madewell. Top, J. Crew. Jacket, Banana Republic. Necklace and brooch, Vintage.

Winter Hat: Kristin MacDonald, Doll Parade

Kristin MacDonald, 27
Fredericton, NB | Doll Parade

One thing I love about living in a part of the world with 4 distinct seasons is that every one of them brings along a new set of accessories. And what I have come to realize about this nonchalant head piece – the beanie, or “toque” for us Canadians – is that it can quickly pull together just about anything (even me when I was feeling particularly dishevelled). Beanies are unisex, though their punch can lie in the details. Mine here is a vintage angora (don’t worry, they take the bunny’s moulted fur, not their life!), and I’ve also fallen deeply in love with the Stephen Jones veiled beanie for Jill Sander. And though I’m also supremely into the wide brim fedoras that have been floating around the blogosphere, choosing this more relaxed looking hat didn’t leave me with flat hat hair as the day wore on. Yes and yes.

Winter Hat: Alicia Quan, Alicia Fashionista

Alicia Quan, 25
Vancouver | Alicia Fashionista

I’m very thankful for the mild winters we get here in Vancouver. And though we’re able to avoid a ton of snow, we definitely endure a ton of cold, soggy days instead. My favourite defence against the West Coast winter elements is a large brimmed felt hat. It manages to keep my head warm, as well as protect my hair from the rain. An oversized winter hat is basically the perfect compromise between practical and trendy. In order to keep warm, I also pair it with essential winter accessories like a big scarf, gloves, and boots.

Alicia’s wearing: Blazer, Chevalier. T-shirt, Gap. Shorts, Aritzia. Hat, Front and Company. Scarf, Forever 21. Boots, Dolce Vita Joust. Bag, Urban Outfitters. Bracelets, H&M.

Winter Hat: Kassandra Camponi, Kastles

Kassandra Camponi, 26
Edmonton | Kastles

Whether I like it or not, winter seems to stick around for a very long time here. It starts early and leaves late. One has no choice but to embrace it. Embracing it includes accumulating a large collection of hats, scarves, mitts and coats (which is easily justifiable since I “need” all these items).

It is quite easy to wear these items and still look stylish. I find a lot of people like to buy winter items in basic colours such as black or grey. It tends to get a bit depressing after awhile. I like to mix things up and add a little cheer to my winter wardrobe by picking bright or patterned items, like this neon green beanie. Since this beanie is part of my ensemble, I usually leave the hat on while I am inside as well. This way I can avoid “hat head”. If you are afraid of hat head, there are also a lot of cute headband options out there. I find the knit headbands to be a little easier on the hair.

Kassandra’s wearing: Hat, blouse and necklace, Joe Fresh. Top, Zara. Skirt, Motel Rocks. Blazer, Urban Outfitters. Booties, Kenneth Cole Reaction.