So this article mostly applies to people who live in places that get rougher winters. When I’m talking about a rough winter, I’m talking about place where it’s not too unusual to see single degree Fahrenheit temperatures or negative degree Celsius temperatures during Winter.

The main takeaway from this article is that you don’t have to sacrifice too much in the form of style to get function out of your garments.

Personally, I err to the side of function rather than style, and that’s typically how I style my clients as well.

Winter is actually my favorite season style-wise because I get to play with layers (eventually I plan to also make an article on layering.) Also, like I said, balancing that thin line between function and style makes things interesting as well.

A lot of people have difficulty doing that, so if you can do it yourself it really elevates your outfit.

So these are the essentials, these are things you’re going to want to have:

  • A Real Winter Coat
  • Gloves
  • Snow Boots/Overshoes
  • Base Layer Pants
  • Sunglasses (Yes, Sunglasses)

These are things you may want to consider (if you plan on spending quite a bit of time in the cold):

  • A hat
  • A scarf
  • Thick wool socks

A Real Winter Coat

So in terms of a real winter coat, you can’t go wrong with a down parka.

When I say down I don’t just mean feather down I mean synthetic down as well.

Why a down parka?

  1. They look great
  2. They keep you warmer than just about anything else (especially because of the fur trim)

Puffer jackets, pea coats, and top coats are fine as well if you don’t mind having to wear a hat sometimes when the temperature is especially brutal.

One thing about pea coats and top coats: If you don’t size them properly, if they don’t fit your body, or if the rest of your style isn’t on point, you might risk the chance of looking like a dork wearing one.

You only want to go with pea coats and top coats made out of wool:

  1. It looks so much better than synthetic crap and
  2. It’ll keep you so much warmer. Polyester isn’t going to keep you warm

Another thing: If you think because you wear suits or blazers a lot that you need to go with a pea coat or a top coat, you don’t.

You can wear a puffer or parka over a blazer or suit as long as it’s not too crazy. Some traditionalists might disagree with me, but hey, they can eat it. I disagree with that sentiment. I disagree with a lot of things traditionalist think.

I think wearing other types of outerwear except the aforementioned when the temperature is especially brutal is kind of silly.

A lot of jackets and outerwear don’t cover your thighs and legs and that actually makes a pretty noticeable difference in the cold.

In terms of recommendations, I’m a huge fan of Alpha Industries and I’ll shill that brand until the day I die.

Uniqlo isn’t a bad option either if you’re on a budget,

A lot of people either buy or recommend Canada Goose, but it’s not a very economical option. While Canada Goose does have natural goose down in their parkas, you’ll find that the North Face and Eddie Bauer both have natural down as well at a fraction of the price.

I guess the real selling point of Canada Goose would be the actual fox for trim. While it does look a little nicer than synthetic trim and keeps your face a little warmer than synthetic trim, in my opinion, it’s not really worth the extra hundreds of dollars.

Another thing is: everybody and their mom (almost literally) in metropolitan areas wears Canada Goose. So it’s just pretty, for lack of a better word, basic to me.

If I wanted to spend four digits on a single article of clothing I would just go all the way and instead of getting a Canada Goose parka, I would get something from perhaps Gorski or another high end clothier instead.

Like this one right here.

You can do better than Canada Goose. You might even want to consider a brand like Moose Knuckles.


Gloves are so incredibly important. Your extremities get cold way faster than the rest of your body in frigid weather.

Cool thing: Maybe you’re already hip to this. I wasn’t so hip to this and I found this out recently, but now even actual leather gloves (made out of real leather, not the bonded crap or pleather) are touchscreen compatible. So that’s pretty cool. Especially if you need to call a Lyft or an Uber or something.

Moving back to extremities getting cold way faster than the rest of your body: I’m particularly sensitive to this.

If my hands aren’t properly insulated and I’m in the cold for too long my body could be sweating while my hands would be an incredible amounts of pain from the cold.

An example of why protecting your extremities is so important: One day when it was especially bad outside, around -10 degrees Fahrenheit, I was walking home from the bar and despite having gloves on and another layer of gloves underneath, I still almost got frostbite. You can only imagine what could’ve happen if I didn’t have gloves on.

Snow Boots And Overshoes

There are a few problems with wearing typical leather shoes or boots in inclement weather.

I’ll start with the biggest one: moisture and salt absolutely tear through calfskin leather.

It’s crazy, they demolish it.

Some people will wear a Cordovan leather in the winter and just be really good about wiping the salt off but I personally wouldn’t recommend doing that either.

Another this is: even with rubber soles you’re not going to get the same traction on snow and ice as you would have with overshoes or snow boots.

If your shoes have leather soles you can forget about having any form of traction whatsoever.

In terms of the choice between snow boots and overshoes, I prefer snow boots. While overshoes will protect your shoes from the elements, they provide no warmth whatsoever.

Another reason I prefer snow boots is dealing with over shoes just creates more hassle and complexity.

I try to be super simple with my wardrobe. I wear loafers and slip on sneakers on purpose just because I don’t feel like tying my shoes.

I’m not saying you have to do that as well but that’s how I am personally. I’m not a fan of unnecessary hassle and complexity.

Snow boots don’t have look ugly either. While L. L. Bean is known for their duck boots Sorel makes them as well and they definitely have way better looking colorways than L. L. Bean does.

If you think these are ugly you have objectively poor taste.

Base Layer Pants

Not much to say here. Absolute game changer.

I don’t really notice a difference in how cold I am with a base layer top on, but there’s a huge difference when I have base layer pants on.


Sunglasses are actually more important in winter than they are in summer. This is because snow is super reflective and reflects a ton of UV light. This reflected UV light can give you a eye condition called photokeratitis, which is pretty much an sunburn of your eye.

I don’t know about you but I don’t really want to have a sunburn on my eye.

The one thing you need to make sure of is that your sunglasses actually provide UV protection.

If you’re wearing, for the sake of example, fake Ray-Bans, sometimes the lenses don’t actually provide UV protection.

Things You May Want to Consider If You Plan on Spending Quite a Bit of Time in the Cold

A Hat

I’m going hatless this winter since the faux fur trim on my parka does a good enough job of keeping my head warm DURING the limited amounts of time I’ll be spending in frigid weather. I’m also growing my hair out.

If you don’t have some sort of trim on your outerwear, you have short hair, or you plan on spending extended periods of time in the cold, a knit hat might not be a bad idea.

A Scarf

Another case of my parka basically taking care of everything. Again if your outerwear doesn’t conceal your neck properly or you plan on spending extended periods of time in the cold this may not a be a bad idea.

Bonus: You can also wrap your scarf around your mouth as a makeshift baclava

Thick Wool Socks

Destroy cotton socks when it comes to keeping your feet warm. You can double them up when it’s extra cold outside.

Mind you, when I say wool socks I mean the kind that look like normal crew socks not dress socks.

Bonus Pro Tip

This may seem obvious enough but you can upturn your collars for extra wind protection.

Not much use on a parka but awesome for top coats and pea coats.

Not gonna lie I feel pretty big brain and sophisticated when people see me turn my cardigan collar up when I go outside in the cold and then turn it back down when I go inside.

Thank you for reading.