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5 Unforgettable Winter Essentials for Men in 2020

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Last year, Punxsutawney Phil the groundhog predicted an early spring.

Phil was wrong, but he’s 130 years old so I’ll give the woodchuck a break.

If the short autumn was any sign, we’re in for another long winter.

We still have a few more weeks until the chill fully sets in across the country, which is just enough time to build up your wardrobe so you can look good and stay warm all winter long.

Do you have these five winter essentials? Check out our recommendations and deck yourself out for the frosty future.

Quick Summary

  • mott and bow olivers

    Heavy Raw Denim

    • We love the raw Oliver from Mott & Bow
    • Awesome home try-on program
    • The heavy fabric keeps your legs dry and warm
  • thursday boots captain


  • everlane parka

    A Heavy Coat

    • A hooded parka like the one from Everlane is great for beating the weather
    • The wool coat is a classic and can be paired with just about anything
    • Usually an expensive buy, but lasts for years and years
  • red mizzen and main pullover

    Mid and Base Layers

    • Mizzen + Main Quarter-zips and vests will keep you warm in winter and last into spring, too
    • A solid henley is one of our favorite bottom layers for winter
    • Mid-layers are what you showcase when you take your coat off
  • mott and bow beanie


    • Keep that noggin warm with Mott & Bow’s Ribbed Beanie
    • Many different styles available
    • You have to leave it on—beanie-hair isn’t a good look

3 Things to Consider When Buying Your Winter Essentials

1. You Can Repeat In Winter

Unlike with the other three seasons, you can get away with repeating staples like an overcoat and jeans several times a week.

Because of this, I always invest a little more into high-quality products.

When it gets cold, you’ll be wearing your heaviest coat every day. It’s not like anything else in your wardrobe, which gets one or two wears per week at most. While dropping a chunk of change on a coat might seem hard, when you think about how often you wear it, year after year, it’s really one of the highest-value items in your closet.

2. Water Resistance is More Important

Water-resistant clothes are always a good call. But in winter, wet clothes can send a chill through your body that only ten gallons of hot chocolate can cure.

If you’ve ever gone through a full workday with wet socks, you know how much a damp foot makes for a damp spirit.

Getting heavy gauge denim and water-proof boots is the easiest way to avoid wet-feet forever. Seriously, don’t even mess with soggy socks. It’s just too sad.

3. Darker Neutral Colors Are More Versatile

When you’re buying higher-ticket items, make sure they match with most of your wardrobe. You don’t want to buy a jacket you can only wear once-in-a-while. Go with darker neutral colors.

By staying dark, you allow more room for layering. As a general rule, you should always layer from light to dark. When you want to add a unique pop of color, let a flannel or button-down do the talking.

And the same thing goes for your legs. Keeping it dark with raw denim just ensures that you have the option to wear your favorite jeans with any outfit you want.

5 Winter Essentials for Men in 2019

1. Heavy Raw Denim

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What we like:

Heavy raw denim is a winter essential for a few reasons. Our favorite pair is the Oliver from Mott & Bow.

We had the chance to review Mott & Bow a few months ago and were really impressed with what they had to offer. They’re a great value and appeal both to the denim-heads and regular guys out there who just want to look good.

Why you need them:

The Oliver is made with 13oz denim which is on the heavy side of what you can commonly find. A pair of thick jeans not only keep your legs warmer, but they also keep the water away from your shoes. There’s nothing as bad as wet socks at work, so don’t leave it to chance.

The 13oz denim also has a lot of structure to it, so it ‘breaks’ rather than ‘draping.’ If you’re wearing these jeans with a parka or anything bulkier, you’ll still look trim and put together.

How to style it:

Raw denim is dark and neutral, so it’s super easy to fit into your winter look.

Here I’ve paired my Olivers with a quilted jacket from Western Rise and Sperry Topsider duck boots. The jeans have a wide enough leg-opening to cover the boot without flaring a ton like a boot-cut jean.

model walking up steps in mott and bow jeans and boots

I still opt for slim fit jeans, even in winter. With all the extra bulk you get from layering, it’s a good idea to keep a trimmer profile where you can.

2. Boots

What we like:

It’s hard to imagine going through winter without a set of boots. While I like Chelsea boots throughout most of the year, I like to go a bit bulkier in winter with something like Thursday Boot Co’s Captain.

This classic work boot is a great option for most days, but when it gets rainy, snowy, and slushy, you have to bump it up to a specialized boot. That’s when I go for Sperry Topsider duck boots.

Sperry Topsiders look great, but more importantly, they keep your feet dry and warm.

Both work boots and duck boots offer pretty good traction, so you can go with either if there’s ice outside.

Why you need them:

I don’t want to repeat myself, but do you really want freezing feet all day?

The case for duck boots is clear—you need to keep your feet away from the elements.

With work boots, you’re getting a style that looks great throughout the year. They may be too warm at the height of summer, but you’ll have no shortage of chances to wear them through spring and fall.

How to style it:

Boots and jeans are an unstoppable combo throughout winter. You saw above how Mott & Bow’s Oliver worked with the Sperry Topsiders, and they work equally well with the Captain from Thursday.

Go with a chestnut or red-oak toned boot for more versatility. Black boots look great in winter outfits, too, but they’re a bit dressy to call true “essentials.” When it comes to “must-haves,” I usually tend toward items you can wear with most of your outfits.

3. A Heavy Coat

What we like:

There are two major items that get us dudes through winter: the parka, and the wool coat.

You don’t need both, but you need at least one.

But a coat can be a major investment. I always recommend saving up for quality here, because you’re going to wear this jacket day after day for a good portion of the year. And you’re going to do the same next year.

Everlane always does a great job balancing quality and value, and they’ve got a great winter staple with their ReNew Long Parka.

everlane renew parka men olive

Why you need it:

C’mon, man. If it’s not obvious why you need a heavy coat for winter, just go stand outside for five minutes.

Beat the rain, snow, slush, hail—whatever this winter’s going to throw at you. For rainier climates like Portland and Seattle, you need something with a water-resistant coating. For the midwest, north, and east coast, you can get by with a heavy wool coat.

How to style it:

Black or navy are both great choices here. Because you’ll be wearing this coat several times a week, make sure you buy something that goes with your whole wardrobe.

Black and navy happen to have that effect.

Stay away from louder looks because they’re less versatile and chances are you’ll get sick of them after a few weeks.

If you are desperate for a pop of color, pick up a rain shell—something you can wear when the weather gets wet.

4. Mid and Bottom Layers

What we like:

The layers are where it’s at. When you take your jacket off, you should look just as good as when you had it on.

What’s the point of pairing great jeans with a great jacket if you’re wearing a raggedy sweater underneath?

The quarter-zip is a classic. It works through fall, winter, and is great even into spring. Yes, we’re already looking forward to warmer weather.

And vests are like the Batman of the fashion world—they’re the wardrobe item you need, not the one you deserve.

Of course, I’m kidding—you obviously deserve one.

Why you need them:

Having a solid mid-layer will keep you warm enough so you don’t need to put on a massive bulky coat, plus they look great when your coat is off. We tried the mid-layers from Mizzen+Main and we’re big fans.

Mid-layers are a great purchase because they work year-round. Even on cooler summer nights.

How to style it:

winter essentials men model standing with coat jeans and vest

Here I’m showcasing a long sleeve henley (killer base layer), and a Mizzen+Main Performance Vest under a lightweight coat. The jeans are Mott & Bow.

I’m able to wear the lightweight coat because the vest and the thick henley add tons of protection from the cold.

Even though this is a casual outfit, the heavy-weight raw denim makes it look rich.

5. Beanie

mott and bow beanie

What we like:

How do you take your beanie? Lump at the top? Lump in the back? No lump at all?

I’m in North Carolina, so even on the coldest days, I can get away with not wearing a beanie. But when I go and visit Virginia, forget about it—the beanie is on.

It’s hard to beat how warm and comfortable these are. Plus, beanies can be styled in a ton of different ways. It just depends on your taste. I like Mott & Bow’s Ribbed Beanie.

Why you need it:

Keep your brain warm. Plus, think of your ears. They need comfort, too.

Even a thin beanie is enough to keep your head warm, but if you want to crank the coziness up to 11, get a thick cap. Bonus points if it has the cotton pompom on top.

How to style it:

Again, you can’t go wrong with black. But you can feel free to indulge in some self-expression with your beanie.

Bright colors, loud patterns—the world is your oyster.


Did you go down the checklist? Have everything you need for winter?

These five essentials will keep you warm and styling throughout the winter. Even better, the jeans, mid-layers, and boots will keep working for you all year.

If you’ve got your essentials covered all you need is a sled, hot cocoa, and a pair of gloves for when it’s time to make a snowman.

You’re all set. Now go out and enjoy the cold weather. You’ll be dreaming about it in another six months.

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