I Live In The 2nd Coldest City On Earth; Here's How I Ride Out Winters In Style

Winnipeg, Canada is literally the second coldest city in the world, and it lost the number one mantle a few years back only because UlaanBaatar, Mongolia grew a lot.
Publish date:
March 1, 2015
coats, weekend, outerwear, outfit ideas, Winter Dressing, Winter Trends

This is the part of winter where for me everything stops being fun. My brain forgets that warm sun on bare skin is a possibility in life, pictures of grass and trees are legitimately, unnervingly nostalgic. And yeah, it's now March — but that makes it worse. There's a cumulatively nasty effect that comes with months of sunless freezing.

I am from Winnipeg, Canada, which is literally the second coldest city in the world (and it lost the number one mantle a few years back only because UlaanBaatar, Mongolia grew a lot). I am an expert on winter by necessity. As I type this, it is -8°F before the windchill. Twenty-five sounds like summer to me right now.

Much of North America still has subfreezing temperatures, plus 85% of the Great Lakes have frozen over, so maybe you're having persistent mid-winter blues, too. And maybe you're like me (and like Kelly here) and the shapeless, sexless tendency of winter clothing really doesn't make you feel that good about yourself.

With that I say: What an optimal time to re-do the wardrobe. And not just as a nice way to lift your spirits when you can't fly to Cancun like your boss — this is the best time to load up on winter clothes, cheapos! The last of everything is on sale. Fellow Canadians, you know Target is liquidating. Re-do your winter duds now and not only will you ride out of winter with class, but you will love yourself in nine months when the cold comes again. It even falls under that adult term investing.

I am a six-foot, broad-shouldered, femmy transsexual; I hate looking sexless, I like to wear pretty things, I would rather sport frostbite than a ski mask for the sake of my mental health and I've had the brittle ears to prove it. (Just kidding.) (Or am I?) Even in the second coldest city in the world, I've found a lot of ways to prevent my seasonal gear from contributing to my seasonal dumps. My recommendations on how to bundle nice:

Get The Best Coat Of Your Life

The coat is the marriage partner of the winter outfit, to paraphrase that motivational quote. It determines 90% of your happiness or misery.

Most coats built for bleak temperatures are the opposite of flattering. I grew up wearing those neon-spacesuit/Michelin-man jackets, which I hated then and hate now. But then two years ago I found this coat on the Internet and fell in love.

And I am still in love with this coat. (And the coat you are in love with two years later is the coat you love for life.) It's feminine, form-fitting, looks good on my long arms and big bones, and with fleece lining and faux shearling fur it's deceptively, incredibly warm. With a tight double-knit sweatshirt underneath, I can walk around in temperatures down to -40°F, which is not a typo.

The important thing is that even on those depressed, late-to-work, eyeliner-in-the-car, I-am-so-ugly-no-one-will-ever-love-me days, I never to fail to feel better in a small way every time I put on this coat. It is comforting in every sense of the word, and it is wonderful. A winter coat is something you put on multiple times a day for up to four or five months: If you feel bleh about it, you'll feel that hard. If you love it, you'll feel that hard, too.

I spent a hundred bucks on this coat that I barely had at the time and it was worth every goddamn penny. Find the best-looking coat of your life and everything about winter gets easier.

Finally: If you are in love with a coat but it's not warm enough to wear on its own, invest in thermal undershirts (you can get them sleeveless too) and/or the aforementioned double-knit sweater.


Sometimes people are incredulous that I wear skirts and dresses in frigid temps — legs are tough! Tights are the second key to winter outfits. Arm your torso and extremities (see below re: boots) and even regular paper-thin tights will be doable in moderately chilly temps. And thicker/sweater tights can easily get you to -10°F and sometimes colder.

A nice warm pair of durable tights are about as pricey as a cheap pair of pants, and they last forever if you're careful with them. Even patterned sweater tights, like the ones I'm wearing in the above picture, are surprisingly toasty.

Also: The best part about wearing tights in winter is that nobody else does it unless you're in New York or DC or one of those militantly fancy-pants cities. Stand out with your fabulousness.

Hats (or not)

Everyone knows you lose most of your body heat through your head. This is why everyone wears padded hats in the winter that make the wearer appear to be either a) a chef or b) a bowling ball.

Fortunately, there's an upside to that "lose-all-your-heat-through-your-head" fact: It's total bullshit.

This makes sense when you think about where frostbite hits first: your scalp's not going to turn crusty and fall off. It's your hands, feet, and ears you have to worry about.

This winter I ditched the padded bowling ball (known to us Canadians as "tuques") that had always been a seasonal reflex. I was surprised how much I didn't miss it. Bad wind and extreme temperatures are exceptions, of course, but a stylish and decidedly non-winter hat can often adequately protect your head, too. (An unfortunate amount of Winnipeg men have figured this out re: fedoras.)

As for when frostbite is a real risk? Consider the earmuff, which always looks cuter than expected.


If there's one article besides a coat that's worth sinking extra money into, it is a nice and warm pair of boots. Not only do you lose heat through your feet, but it's my experience that the more insulated your footwear, the more your legs can stand. If your feet are cold, all of you will be cold. Remember how everyone made fun of the girls who wore skirts and Ugg boots in 2005? Those bitches were warmer than you think.

I wear Sorel Caribou Wool Boots (men's brand because my shoe size is one thousand). These shit-kickers are not delicate nor cheap, but the trim of the wool lining gives it a softer look, and again with the warm down to -40°F. A wool lining is necessary for only extreme winters, in my opinion, but it doesn't hurt, and boots with felt lining can go a long way in subfreezing temps too.

Arm warmers with gloves

You know those thin, lovely-looking, dainty winter gloves? Made out of some mindboggling material that would keep your fingers warm and beautiful in an avalanche? And that cost a month's worth of groceries?

I've never actually worn them, even when I could afford them. Because gloves get lost. Gloves always get lost. (As you can see in the picture above.) If you are a responsible glove-keepers then my stylish hat is off to you, but I don't think I'm alone here. As I type, the lost-and-found at my day job is overflowing with a zombie-invasion-grade number of lost little digit warmers, many of which do not look like they were paid for with pocket change.

So what I like is the dollar-store glove (usually about seven times a season). Match them with a sturdy pair of arm warmers and they not only provide warmth, but then you've got a nice opportunity for patterns and colors on the hands. Arm warmers only look silly when they don't end inside a coat.

Sure, I do have a pair of tough thick mitts. But I only use them on truly frigid days or when I know I'm going to be outside for an extended period of time. Thankfully, I haven't lost them yet.

Sometimes it's hard, in the gloomy winter, to recognize the very real effect that looking nice has on my mental health. The default of cocooned frumpiness is an easy one to fall into. Are there more ways to improve the frozen-winter outfit? Let me hear it! But trust me on getting the best coat of your life.