Here’s what I’ve learned about suiting up in cold weather after more than 10 years of experience with wearing cold–weather tailoring.
During the long polar night, I ventured out onto a frozen river. Alone.
The northern lights shimmered above me, and everything was incredibly still.
While I know it might have not been the smartest thing to do, I don’t regret it.
However, over a mile and a half down the river, I noticed that my left foot was starting to get cold.
I soon realized that my left boot had gotten slightly wet from snowshoeing the day before.
I immediately turned around and headed back to the cabin. I managed to get back before frostbite set in, but there was a very real chance I could’ve suffered lasting injury.
While I was equipped with a lighter, knife, and hand warmers (that I quickly discovered didn’t work), I wasn’t ready for wet feet.
Moral of the story — you need to be prepared when venturing out in the extreme cold. Seemingly small mistakes, such as having improper boots, can quite literally cost you your life.
While the stakes probably aren’t going to be quite so high in populated areas, it’s still a good idea to take precautions.
Many men know how to dress casually in the cold — simply through on a parka and a beanie, throw on a pair of gloves, and maybe wear long johns — I’ve seen many a man shivering on the streets in a wholly inadequate suit and tie without appropriate cold-whether gear.
Not only is it dangerous to walk around without a coat, blue lips and bright red hands aren’t a good look.
Level up your comfort and your style game by considering proper professional winter clothes and accessories.
In this guide, I’ll cover what you need to know about how to dress up when the temperature drops.
Let’s start with the foundation of winter dressed-up looks — the winter suit.
Boy, I have a lot to say on this subject! In fact, as I drafted this guide, this section was so in-depth that it turned into a completely separate article.
If you’re serious about upgrading your cold-weather wardrobe, check out this in-depth winter suit buying guide.
Overcoats For The Cold
Perhaps the most obvious way to stay warm when dressed up is to wear a coat. However, with a suit a puffy parka just looks off.
Get the right classic wool overcoat and you can stay warm in sub-zero temperatures.
The warmest overcoats have a fur lining. Faux fur certainly works to add insulation, but real fur will always perform better. If you have qualms about fur, I’d recommend buying vintage. If even the thought of wearing a dead animal, even if it died 50 years ago, makes you feel nauseous, try to find a faux-fur-lined coat.
I will warn you that the vast majority of men’s overcoats available today are nowhere near as warm as coats of generations past. Not only are coats with warm linings super hard to find, the wool itself tends to be much thinner and made with looser weaves.
Another reason modern coats aren’t as functional is that they tend to be shorter — many today have hems soaring high above the knee.
Think about it. A shorter coat means that more of your body is exposed. A long coat, on the other hand, traps your body heat and protects your pants from mud and slush.
While we short men, in particular, will look best with a coat that ends above the knee, I recently acquired a mid-calf-length that I love. It definitely looks more old-school than my other two overcoats, but I don’t mind.
I’m just careful not to wear it with unusual or old-school accessories like a fedora, spectator shoes, or tie bars to avoid looking like I’m wearing a costume (not that I have those accessories anyway, but you get the point).
Some men can certainly pull off the old-timey look without looking like a caricature. It kind of all depends on your personality and your confidence.
Other overcoat features to consider include wide lapels that you can fold across your chest in lieu of a scarf, straps on the sleeves, sleeves cut long, double-breasted over single-breasted button patterns, and a looser cut to allow for several (or many) layers underneath.
I have three wool overcoats — each of different lengths and with different features.
Comparing 3 Different Overcoats
My first overcoat was a mid-thigh length single-breasted black wool coat with functional lapels, a faux-fur zip-in lining, and a hood.
While a hood certainly isn’t a classic overcoat feature, I’ve really valued the functionality, especially for the 4-5 years this was my only winter coat. It has quite literally saved my ears from frostbite when I’ve been caught out in the cold without a hat.
I’ve worn this coat in -40 degree weather, and, with proper layering, felt just fine (albeit a bit uncomfortable) at those extreme temperatures.
My second overcoat was a custom piece from Hockerty. While I don’t recommend the brand, the coat turned out really well.
It reaches to just above the knee and has a double-breasted 6-button design. While this navy coat isn’t as warm as my other two, it’s the most formal out of the bunch.
Lastly, my newest addition is a vintage Donegal tweed piece I picked up in Minnesota a few months ago.
It’s a long coat — dropping well past the knee to mid-calf. It also has a 6-button DB design. It has notched lapels, which is quite rare for a double-breasted coat. Usually, DB garments with notched lapels look off somehow.
I think it works in this case. What do you think? Let me know in the comments what you think.
Boots for Freezing Temperatures
While you can certainly wear dress shoes in the winter (I do all the time), if you’ll be commuting by walking or public transport, boots are a must.
If you’re going to be trudging through deep snow, you probably won’t want to wear a suit. Either way, you’re definitely going to need true snow boots. And that means you’ll need footwear with an insulated lining, a tall shank, and excellent traction.
However, if you need a boot for city living that can handle the cold and snow, there are some suit-compatible options.
Living in Russia, I had a pair of leather service boots that had laces, but also a zipper on the side. That was convenient! Those boots had a faux-fur lining too, as well as pretty good traction. I’d recommend boots with those features!
Combat boots are another option. Years after I lived in Russia, I spent a couple of winters in the Nordic countries. I tested out Thursday’s Explorer Boots during that period. (I eventually gave them to a friend in Buffalo, NY).
They were excellent in for city use, but definitely not cut out for use up above the Arctic Circle (you’ll find out why later on in this article).
If you live in NYC, Boston, or Chicago, consider these boots.
Layering for Extreme Cold
Layering is an essential component of cold-weather dressing no matter the formality.
Often when suiting up in the winter, I don’t need to think too much about layering as I’ll be inside a heated building. Wearing a heavyweight suit with a substantial overcoat along with a few winter accessories is enough.
However, if I’ll be outside for longer than a few minutes layering becomes critical to my comfort and safety.
If you’re wondering about layering from a style perspective, read this article.
The foundation of winter layering are your baselayers.
While I prefer synthetic materials here, wool works too.
Long-sleeved undershirts take many forms. You can experiment and choose what works best for you.
Up top, I might wear a compression shirt and on the bottom, running tights.
I find that running tights are quite a bit warmer than standard long johns (they’re pretty much the same thing, running tights are just thicker and have more features as they can be worn as an outer layer when running).
In extreme cases, you could wear long johns and running tights underneath your suit pants.
Socks for Bone-numbing Temperatures
As you’ve probably guessed, this situation calls for thick wool socks. You might even want to wear two pairs.
While it would be ideal to wear socks that are as similar to dress socks as possible, it’s more important that you’re warm. You’ll mostly likely be wearing boots so no one will see you’re socks anyway.
Mid-layer (Dress Shirts)
As a mid-layer, you’ll probably want to wear a dress shirt.
If you do, you can benefit from choosing a thicker cotton than usual, but, honestly, it’s fine to wear what you would normally. Your other layers will do the heavy lifting in keeping you warm.
In lieu of a dress shirt, you could choose a slim-fitting turtleneck sweater.
Besides having the added benefit of protecting your neck, a wool sweater is more insulating than a cotton shirt.
After you’re wearing your base layer (s) and your dress shirt, it’s time to put on your suit. As I’ve already discussed winter suits above, there’s no need to expound more here.
Now finally it’s time to slip into your overcoat. Make sure that you’re ready to leave the house before putting it on — you don’t want to overheat and start sweating.
Like Survivorman, Les Stroud, always says “If you sweat, you die.” (While perhaps that’s a bit melodramatic in most cases, you definitely don’t want to be sweating when it’s -35 degrees).
Check out my guide to overcoats for more info.
I’ve found that proper winter accessories often are the difference between cold and miserable and being comfortable in frigid conditions.
You lose a lot of heat from your head so it’s vital to wear a hat if you’ll be outside for extended lengths of time.
While you can choose a wide-brimmed hat, like a fedora, it’s not a top pick for me. For one thing, I don’t think I could pull it off without looking like a cartoonish caricature of a 50s mobster. Besides that, you want to keep your ears covered.
A regular run-of-the-mill beanie does the job in a pinch, but it’s an inherently casual piece. I’d recommend trying to find a winter hat that’s a little more structured. This winter I’ve found myself wearing this watchcap often with my wool overcoats.
It’s comfortable and pretty warm. I can actually adjust the band to cover my ears, and there’s a hidden earflap tucked inside (though when I use it my friends say I look like a medieval peasant).
When it’s truly, seriously cold, you can’t do any better than a fur hat. I got mine years ago in St. Petersburg, and I’ve worn it at least a couple of times every winter since.
Will you look out of place outside of the former Soviet block?
Of course you will.
Will your head be toasty warm even when it’s -40 out?
Of course it will.
I’m not recommending that you buy one, but I’m not saying you shouldn’t either 😉 .
Americans men don’t like scarves. That’s a generalization, I know, but I’ve found it to be mostly true.
In Europe, scarves are ubiquitous. Maybe it’s the stereotypical European knack for fashion talking, but I have a theory that it’s because Europeans are more likely to walk or take public transit than us Yankees.
While you may be the only guy in your friend group wearing one, consider wearing a scarf. (Especially if you already stand out by wearing a formal wool overcoat and a suit).
I’ve noticed that scarves are especially useful for keeping my chest warm and dry when I’m wearing an overcoat that doesn’t button all the way up to the top.
When buying a scarf, pick wool instead of cotton or acrylic (wool insulates even when wet).
Not only should you think about keeping your neck warm, your hands need to be covered up too.
Cashmere-lined leather gloves are the classic dressing-up-in-winter option.
However, there comes a point when even these are insufficient.
That’s when it’s time to switch over to mittens.
Mittens are warmer but decrease dexterity.
It’s difficult to find mittens that look great with a suit or formal overcoat, so when it’s super cold I just wear my black sportswear-style mittens.
Other Cold-Weather Tips
Here are some other tips I’ve learned during my travels to cold climes:
If you spend a lot of time outdoors, you might want to invest in a quality pocket warmer. These are common among hunters and outdoorsmen.
I personally like the Zippo Refillable Handwarmer, but there are a lot of options out there.
My favorite alternative to a refillable hand warmer is the incredible, edible pocket potato.
I’ve mentioned this “hack” before on the site, but what you can is wrap two raw potatoes in aluminum foil and put it in the oven until they’re hot but not cooked.
Then, you put them in your coat pockets before you head outside.
You’ll feel like the richest schoolboy in the Great Depression!
You’ll have an hour or more of warmth, and, as an added bonus, a snack for later! (Assuming unseasoned half-cooked potatoes are your thing).
Stay Dry, Don’t Die
I know I’m beating a dead horse here but this one is so very important. When it’s very cold outside it is absolutely critical that you stay dry.
You might not feel uncomfortable at the moment, but once your core body temperature inevitably drops back to baseline you’ll start to feel a chill. Without seeking warmth and shelter or otherwise changing into dry clothes, your body temperature will continue to plummet until you reach a hypothermic state, which in turn eventually leads to death
Following the “don’t die, stay dry” mantra may lead you to act counterintuitively. For example, the other day I was shoveling snow in the bitter cold and, after a few minutes of exertion, I took off my overcoat. Why? Because I was starting to overheat.
Admittedly, there’s little danger of becoming hypothermic in my driveway (I can always just go inside), but I don’t want to get in the habit of allowing myself to get wet in the cold.
Similarly, I highly advise that you don’t let yourself get wet in cold weather, even if you’re just jogging down the street to get a cup of coffee on your lunch break.
Protect Your Cheeks
Below about -15 or so you’re going to need to cover up your face. You can use a thermal neck gaiter, but I find that a scarf works well too.
Simply wrap the scarf around your neck a few times and tuck in your nose and chin.
Never Sacrifice Style for Function in the Extreme Cold
My final piece of advice is that when it’s below zero, don’t worry so much about how you look. Few people will pay attention to if your mittens match the color of your boots when their eyelashes are starting to freeze up.
It’s much more important to stay safe, and warm, than it is to look like a J.Crew model.
What’s the coldest temperature you’ve worn a suit in? Let me know in the comments!