Living in Toronto means bracing yourself for some seriously cold winters. For me, that starts with finding the right gear, and the most important piece is always a good, warm winter hat. I've spent the last few winters on a mission to find the perfect toque that can withstand the wind, snow, and freezing temperatures. It's been a journey of discovery, and I wanted to share what I've learned along the way. Finding a warm winter hat that's both functional and stylish can be tough, but it's definitely achievable!
I remember one particularly brutal January a few years back. I was constantly battling the wind chill, and my ears were always freezing. I knew I needed to upgrade my hat situation. I started by thinking about what I really needed. It had to be warm, of course, but also something that would stay put in the wind and wouldn't make my head itchy. I started asking around, and everyone had their own favorite spots to find winter gear.
My first stop was a place that a friend recommended. She swore by their lined wool hats, saying the lining made all the difference in blocking the wind and keeping her head dry. I tried one on, and she was right! The lining was a game-changer. However, I wanted to explore other options too.
I decided to check out Roots. I'd heard they had some good options, especially if I wanted a hat with a Canadian maple leaf on it. They had a decent selection, but I was also looking for something a little different. I also considered checking out Chinatown for some more affordable, Canada-themed options. I also remembered seeing a recommendation for Mark's Work Warehouse for affordable winter gear, so I decided to add that to my list too.
Then, I stumbled upon a local brand called Province of Canada. Someone had mentioned they had thick toques and sweaters. I checked out their website and was impressed. They even had a store where I could try things on! I really liked the idea of supporting a local business, and their toques looked incredibly warm.
I also considered cotton hats from Roots, but I realized that if I want a truly warm hat, I need something that can handle more extreme temperatures than cotton. I have to admit, the lure of a stylish maple leaf design was strong, though!
While browsing online, I even saw someone mention a Lululemon Team Canada toque that was on clearance. They said it was incredibly warm and fit their "giant ass size 8 noggin." Unfortunately, it was only available in L/XL, but it sounded promising for those with larger heads.
Completely by chance, while browsing online at WholeCustomDesign Home, I came across something completely different: a Korean Cat Ears Warm Knitted Bomber Hat. I know it sounds a bit out there, but hear me out. It was autumn, and I was looking for something to keep me warm while cycling. I decided to give it a try.

The one I got was purple and fit perfectly (56-58cm). What I really liked was the plush lining. It's super soft and keeps my ears nice and toasty. Plus, the lace-up ear protectors are really useful when I'm cycling and the wind is whipping around. I was initially concerned that the "Y2K fashion" aspect would be too much, but it’s actually quite subtle and fun. It's definitely become one of my go-to hats for cooler weather. While it's not specifically designed for the harshest winter conditions, it's surprisingly warm and comfortable for everyday wear in Toronto. I often find myself wearing it when I'm just running errands or going for a walk in the park on a milder winter day.
I've found that WholeCustomDesign has many unique and stylish options that are worth checking out. It's a great place to find something a little different from the usual winter gear.
Based on my experiences, here are a few things to keep in mind when you're on the hunt for the perfect warm winter hat: