There’s one thing that us former tropic natives and style aficionados like about Toronto, and it is that the four different seasons give us a chance to vary our attire. In the summer we can continue to wear shorts and sandals and light, short-sleeved shirts and polos, but we can also wear scarves and sportcoats in the winter.

Some of us take the task quite seriously, squinting at GQ articles, asking questions and studying the outfits of well-dressed people (discreetly, lest they think we’re about to hit on them). In the process we usually find, much to our surprise, that many Canadians don’t take winter attire seriously. In Europe, I often saw men wearing scarves, leather gloves, and stylish but warm boots, yet many guys at UTM wear gloves the size of boxing gloves, sneakers with slippery soles and Santa Claus hats.

Given that autumn forgot to show up this year, I thought it was about time I write up a list of tips on what to wear for the winter. It’s not because I know better than you or that I think I’m more elegant, but because there is certain irony to a Cuban writing about winter attire in a Canadian newspaper. And also, you might find something useful. (Or I might, if some of you decide to write back with tips).

An authentic fur trapper hat will make you look cool, just like this guy.
An authentic fur trapper hat will make you look cool, just like this guy.


Can’t live with ’em, can’t live without ’em. I regard hats with suspicion, maybe because in the tropics we seldom wear them. (We certainly don’t wear straw hats, unless we’re working in the fields). Plus I hate hat-hair. That said, I hate frozen earlobes even more. Up to 80% of your body heat escapes through your head. I don’t know if that statistic is true, but it certainly feels true on cold days.

Stick to the basics: a toque on really cold days. (Driving caps look good but are not as practical). Felt toques literally stink, so get a wool one, or one in cashmere if you can afford it. And no fuzzy balls hanging from the top, for the love of God, unless your name is Hans and you are a ski instructor.

On really cold days, the bold and the daring can get away with wearing one of those fur-imitation trapper hats. Many clothing brands are trying hard to make them fashionable (they made Ugg boots fashionable, even for some guys, so they’ll probably succeed). A friend at work once remarked that trapper hats look stupid. I can’t help agreeing. He also said they looked warm, and by all accounts, they are, which makes me wonder whether I’m the stupid one for refusing to wear them. In the end, people with trapper hats may look daring, with that screw-you attitude that can, when discreetly done, do so much for your appearance.

Where: Everywhere.
Price range: $20 to $50.


One easy way to tell Canadians from foreigners: Canadians seldom wear scarves. To this day, I have no idea why. Scarves keep the throat warm and fend off colds. They also look great. For those who fear that a scarf will make them look silly, rest assured — they can attract female fingers like a magnet, especially when made of cashmere. (Once you try a cashmere scarf you’ll never go back).

Hemingway wore scarves. Sartre wore scarves. Scarves are manly things. Get one in a solid colour, or perhaps with a few stripes. The simpler, the better. Burgundy is a widely ignored, but a smart choice.

Where: H&M, eBay, Winners.
Price range: $50 to $200.

A nice pair of leather gloves will keep your hands warm and stylish during the winter months.
A nice pair of leather gloves will keep your hands warm and stylish during the winter months.


Gloves are so easy to get right. Yet most guys don’t. All you need is leather. Thin leather gloves will work anywhere, from Frosh to graduation to the job interview, and they are guaranteed to impress your date.

Ideally, gloves should match the colour of your shoes. Go for brown first (you did get those brown boots, right?). Get a second pair in black when you find a sale. And make sure they are lined inside. I have a pair lined in cashmere that I bought at Danier for less than $30. Synthetic lining also works—some say it works even better, but I recommend you pass it up if you have sweaty hands.

According to many forums, the best gloves come from a small workshop in Florence called Madova. They are handmade and retail for up to 60 euros. A bit on the pricey side, but the quality is indisputable. I’ll get them when I make decent money. And when I learn not to lose my gloves.

Where: Danier (waiting for post-winter sales will score you a great price), Winners.
How much: $30 to around $80 for the Madova gloves.

The L.L. Bean Katahdin Iron Boots.
The L.L. Bean Katahdin Iron Boots.


Come wintertime, I see many people tiptoeing around campus with Chuck Taylors or other sneakers. I wonder if they just haven’t tried boots. Boots are warm, comfortable, and allow us to stroll around without worrying about sludge pools. They’re back in style now, especially army boots and old-fashioned boots like the L.L. Bean Katahdin Iron boots (my likely choice), a few Timberland models, and the Wolverine 1,000 Mile Boots, which were first sold in 1914. Even Aldo has taken to selling vintage-looking boots.

As for the colour, I once read that Italian men only wear black shoes when they go to a wedding or a funeral. We should take cue. Black shoes are overrated — and overused. Nothing looks better than freshly polished brown shoes. I tend to agree in the case of boots, although there’s nothing wrong with a nice pair of black ones.

Where: Timberland stores, Aldo, Little Burgundy, Brown shoes, online.
How much: $120 to $300.


Many people think the more stylish the jacket, the less warm. Not necessarily. A wool, wool-and-cashmere or pashmina wool coat can effectively protect you against Toronto’s nastiest winter days, especially if: a) it’s got a warm lining, and b) the front zips and buttons closed. Moreover, longer dress coats protect your legs like no ski or puffy jacket can.

Now, unlike most other accessories I mentioned earlier, these coats are difficult to find at a moderate price. But you never know. I once found a very nice wool-and-cashmere British dress coat at Goodwill for $15. A quick, $10 visit to a trustworthy tailor made the jacket look as if it had been custom-made for me.

For those who need a winter jacket right away, a parka may be cheaper and easier to find (just go for a solid colour).

Where: Tom’s Place, Winners, some department stores. And yes, Goodwill.
How much: $15 (OK, only at Goodwill) to infinity.

  • A

    great article!