Men's Winter Casual Fashion Guide 2020

November 02, 2020

Winter is coming...

And if you’re like us, winter fashion is about keeping it casual and relaxed. 

While this season is sure to see an abundance of sweats, dressing casual this winter does not mean you need to sacrifice style.

With various fabrics, textures, and colors, countless combinations turn mundane layers into sled-stopping outfits that will surely stand out in the crowd of oversized coats, pajama work attire, and the overuse of black and grey outfits. 

This year we’ve put together a comprehensive guide that takes into account more of us working from home than ever to a season full of more at home gatherings. 

In this guide, you’ll learn: 

  • How to elevate sweats and joggers to something more refined so you do not feel like a lazy slob
  • Creating a go-to work from home outfit to feel more productive and get more done
  • Choosing the right pair of boots and shoes that fit your personality and style
  • Winter fashion accessory essentials
  • And much more...


PART 1: How to Dress for Winter 2020 

At the start of COVID-19 closures, we lived in sweats and pajamas. While this initial comfort felt great, soon the overly casual outfit left us feeling uninspired and unproductive.

This winter we will be spending more time at home than ever. We wondered how to bridge the gap between at-home comfortable and not looking like we’ve given up on life.

Without further ado, let’s jump into our versatile, winter wardrobe that not only feels great, but makes us look great too.

1) Trade traditional sweats for Chinos or stretch jeans

Men's Winter Fashion Chinos

We love our sweats and joggers, but they still feel like pajamas to us and make it hard shifting our mindset to getting shit done.

These days we are either reaching for Chinos or jeans with stretch to them.

Chinos offer a nice middle ground with versatile options such as drawstring chinos offering just the right amount of casual, yet dressy enough to not feel like a bum. 

Bonobos offers great options for a traditional Chino or Save Khaki for drawstring chinos.

While your mileage will vary on jeans as it's one of the hardest pants to find the right fit, Levi’s offers solid options for stretch jeans. Reddit Mens Fashion has also said good things about Duer stretch jeans

COLORS: Opt for forest green, navy, black denim, or shades of grey. Or for a bit more flavor, choose vertical stripes or plaid with the same color scheme.

2) But if you are going to wear sweats/joggers, here’s how to do it

Ok, we are all about comfy and cozy this winter and that means sweats/joggers need to come into the equation.

Whether we are just feeling sweats during a workday or want a very casual winter outfit for the weekend, there’s a way to do it with style.

If considering a full athleisure look, consider the plaid tracksuit:

The Gentleman Track Suit Look

Experiment beyond solid black and grey track pants with classic patterns such as plaid. It gives the appearance of a casual suit. In one of the most stylish films of 2020, The Gentleman, they've used traditional English suiting fabrics. It’s retro sportswear that doubles up as high fashion statements.⁠ Pair with a classic white sneaker so as to not distract from the outfit whole. 

Pair with a monochromatic button up or polo to dress the look up further.

For a weekend casual look, consider layering joggers with a hoodie and jacket:  Mens Joggers and Hoodie

Winter is all about the art of layering. Pairing joggers with a hoodie and a bomber jacket or denim jacket is an everyday outfit combo that will always look great. 

For a work from home look, consider pairing with a cardigan or work jacket

Mens Joggers Cardigan

While during quarantine, we’ve seen gents rock a full blown suit, it’s a bit overkill for us. Instead a cardigan or work jacket can recreate the look while maintaining comfort. 

For the shirt underneath, we recommend a sweater or long sleeve t-shirt. If you want to go dressier yet, consider pairing with a classic solid colored button up.

3) Men’s Winter Coats

Mens Winter Overcoat

The Overcoat

Winter is the season to flex all of that outerwear that’s been hogging up space in your closet, and long winter coats are one of our top picks for this year. They protect against the weather and check off the box in the style department. Car-coats (overcoats) provide a casual look for a high-low approach.

Shoot for a patterned wool-blend topcoat worn over a suit to keep you business-ready all day, or wear a classic camel overcoat with a thick tee or sweater and denim to stay casual. 

Mens Parka

The Parka

Being from Chicago, it gets bone chilling cold. When its 0 degrees outside and you are getting blasted with treacherous winds, warmth > fashion. 

But since seeing Canada Goose parkas explode on the scene years ago, designers have stepped up their parka fashion game. 

Now you can choose a wide variety of parkas that offers both functional warmth and looks good too.

4) Layering with sweaters, cardigans, and field jackets

Mens Fashion Winter Layering

(Jacket: Everlane Navy Chore Jacket | $78, Shirt: Everlane Sand Dune French Terry Crew | $54, Pants: Bonobos Grey Glen Plaid Stretch Chinos | $98, Shoes: Marc Nolan Belmont Burgundy Boots | $145)

Fall/Winter is the season about layering. For the most comfort, make sure that the layers closest to the skin are the thinnest and fitted to your body. For all other layers, it can be looser and bulkier for warmth. 

So how should you layer for a casual winter look? 

A classic button-down with a sweater is, well, classic for a reason. It is a tried-and-true style that’s quick to assemble and always looks good. 

Chunky shawl-collar cardigans add a significant amount of bulk and warmth when worn over collared shirts, turtlenecks, long sleeve shirts, and even sweatshirts. Lighter-weight sweaters made of cashmere or merino wool pair nicely under a blazer and add a little flair for an outfit that’s ready for work or play. 

Additionally, Chore Jackets have taken Fall and Winter fashion by storm this year, and rightly so. The name speaks for itself, as these jackets are often lighter pieces that resemble thicker button-down shirts. 

When worn over a sweater or your favorite dress shirt, “shackets” can take the place of a traditional blazer and is casual enough to wear indoors to keep you warm.

5) Winter Men’s Outfit Ideas

Mens Winter Casual Outfit

Work from home: Hoodie + Chinos + Loafers

(Hoodie: Champion Reverse Weave Hoodie | $69, Pants: Save Khaki Navy Twill Easy Chino | $138, Shoes: Marc Nolan Abe Caramel Penny Loafers | $115)

Mens Winter Casual Fashion

Work from home: Chinos + Denim Button Up + Cardigan + Combat Boots

(Jacket: Wallace & Barnes Cable Knit Cardigan | $198, Shirt: J.Crew Slim Lightweight Denim Shirt | $89, Pants: Bonobos Navy Portland Travel Jeans | $78, Shoes: Marc Nolan Aiden Combat Boots | $145)

Mens Winter Casual Fashion

A bit chilly outside: Stretch dress pants + cable-knit sweater + blazer (or field jacket) + Quarter Brogues 

(Jacket: J.Crew Navy Everyday Bomber Jacket, Pants: Bonobos Weekday Warrior Stretch Dress Pants | $78, Sweater: Aran Sweater Market Super Soft Aran Crew Neck Sweater | $115, Shoes: Marc Nolan Vinnie Quarter Brogue Sneakers | $115)

Mens Winter Casual Fashion

It’s cold outside: Wool drawstring trousers + merino wool sweater + lightweight parka + overcoat + boots

(Jacket: Suit Supply Mid Green Overcoat | $599, Parka: Uniqlo Yellow Pocketable Parka | $40, Pants: Suit Supply Drawstring Ames Trousers | $198, Sweater: J.Crew Merino Wool Maried Navy Sweater | $80, Shoes: Marc Nolan Belmont Black Wingtip Boots | $145)

Part 2: Men's Winter Shoes

1) Men's Winter Boots

Marc Nolan Belmont Cognac Wingtip Boots

The Classic Fall/Winter Boot

Just like we think every man should own a crisp white button up, a quality brown boot is a closet staple must. The outfit pairing options are virtually endless from casual to dressy and can fit almost any occasion from light hiking to nights out. 

If you want to move beyond a standard closed toe boot, consider the Wingtip Boot. The full brogue detailing elevates the classic look just enough to add personality to your outfit without screaming, “look at me!”

Marc Nolan Aiden Black Combat Boots

Suede Boots

Suede boots are a great way to add visual interest to your outfit while also looking more elegant than your traditional classic boot. 

Opt for tried and true colors of brown, burgundy, or black for the most versatility. And if you are willing to venture a few more steps outside your comfort zone, our Aiden boots modeled after the Jordan 11 sneakers turn up your outfit’s heat even more. 

In general, the more eye-catching the shoe, keep your upper body style on the minimalistic end for a cohesive well thought out look.

*WEATHER TIP: Use Crepe Protec to waterproof the suede for those wetter/snowier days.

 Sorel Snow Boot

The Snow Boot

For those wet gross days outside, you’ll want to get yourself a quality snow boot. We are partial to Sorel as they are made for Winter and offer a range of warm and waterproof options.

Pictured above is their Cheyenne Metro Lace Boot which is actually a sneaker boot hybrid. They are bit sleeker than your average snow boot. Because of this, you can wear them with regular jeans around the city when needed.

2) Men’s Winter Sneakers 

While there are certainly waterproof, winter-focused sneakers available on the market, for snowier situations, we rather reach for our boots. Rare is the winter focused sneaker that is both functional AND looks good. 

For those non-snowy/rainy days, we much rather reach for a sneaker that stays within the fall/winter color palette. Think browns, burgundy, navy, and yes, old faithful, black.

Marc Nolan Gavin Burgundy Wingtip Sneakers


Gavin Burgundy Wingtip Sneakers offer great versatility for dressing up or down from weekend errands to holiday get togethers. It’s a great shoe that retains the classic aesthetics of a wingtip with just the right amount of modern sneaker updates to keep it comfortable and casual for less formal situations. 

While Burgundy can work year around, it especially looks at home in the fall/winter.

Hybrid Dress Shoe: Marc Nolan Gavin Burgundy Wingtip Sneakers

Marc Nolan Declan Mahogany Sneakers


Traditional sneakers keep the style casual, while elevated luxury details make you be taken seriously. Our Declan line of sneakers are made with classic aesthetics in mind, but with enough personality to not be another boring minimalist sneaker. 

An ultramodern and architectural silhouette is combined with intricately designed intersections and overlay throughout. Made with burnished mahogany calfskin leather, Declan can easily be paired with all your fall and winter casual outfits.

Sneaker: Marc Nolan Declan Mahogany Sneakers

Marc Nolan Ace Cognac Plaid Penny Loafers


While we love ourselves a great house slipper (more on that below), penny loafers kill two birds with one stone to be worn inside and out. Our Abe Penny Loafers in cognac and tartan was built for such a task.

Lush calfskin leather encircles an Italian merino wool contrast panel featuring classic tartan with beige and coffee colors to give these cognac shoes texture and versatility. Pour yourself a glass of whiskey, slip on and chill out. 

Loafer: Marc Nolan Abe Cognac Plaid Penny Loafer | $115

3) Men’s Winter Slippers

Ugg Kenton Slipper

The House Slipper 

We’ve already seen a surge in house slippers at the start of the year and winter 2020 is sure to be no different. When it comes to house slippers, UGG knows what they are doing. Their Kenton slipper with full sheepskin lining will keep your cozy on those snowy winter days. Plus the rear is collapsable giving you options to easily slip on or keep it up for greater support.

Slipper: Ugg Kenton Slipper | $100 

Marc Nolan Odell Belgian Loafer Sneakers

Slipper Alternative: Belgian Loafers

As an alternative to a traditional slipper, consider the Belgian loafer. Once a prominent staple amongst the New York elite, Belgian loafers retain a timeless aesthetic looking simultaenously classic and modern. 

Pictured is our Odell line of Sheepskin Belgian loafers made for house comfort in mind with full leather lining, padded in soles, and a thick white sneaker gum sole for greater functionality.

Belgian Loafer: Marc Nolan Odell Navy Belgian Loafer Sneakers


PART 3: Men’s Winter Accessories Essentials 

Hats, gloves, scarves, beanies, earmuffs—these pieces are getting the most visibility this time of year. From different fabrics and patterns to a range of price points, it is easy to find accessories that fit seamlessly into your winter wardrobe. 

Try a timeless classic like a chunky wool scarf, make a statement with a beanie in a bold color, or invest in the oh-so-luxurious cashmere and leave the house every day knowing you’re protected from the cold and always photoshoot ready.

Love Your Melon Navy Beanie

The Cotton Beanie 

While you’ll see Love Your Melon Beanie’s on the pumpkin spice latte brunch crowd, we can’t help but love em.' 

They are super comfortable, keep your head warm, and are not itchy. Plus 50% of their profits goes to fight against pediatric cancer.

They have a variety of colors and patches, but the monochrome Navy is our favorite. 

Fleece Touchscreen Gloves

Touchscreen Fleece Gloves

Uniqlo’s HEATTECH line of gloves is Lined with fleece that has moisture-absorbing and insulating functions. Ribbed knit cuffs block wind and give them a more casual look. Fingertips are touchscreen-capable so you can use your smartphone.

Uniqlo HEATTECH-lined knitted fleece gloves | $20

Dents Leather Gloves

Leather Gloves 

Want a glove that looks a bit dressier than your fleece knit glove? Consider Dent’s leather gloves lined with a naturally insulating wool blend. 

Dent’s Dark Brown Henley Touchscreen Leather Gloves | $100


Wake Up & Fight Face Mask

The Wake Up & Fight Mask

By now, there are endless masks on the market. We are fans of apron manufacturer Hedley & Bennet’s masks. 

For starters, their masks are made out of oxford fabric giving each a more sophisticated textured appearance. Their masks are adjustable, has a metal nose insert for a better fit, has a inner pocket for an additional filter, and they work with first responders to supply them with masks...sold.

Headley & Bennet Wake Up & Fight Mask 3-Pack | $45


SIDENOTE: Men’s Winter Skincare Tips


Benamôr Gordissimo Nutritive Hand Cream

#1: Use a Handcream

While we can get away in summer without much lotion for our hands, inevitably as the weather shift colder, our hands begin to crack.

We’ve used Aveeno Daily Moisturizing lotion for years and it works great as a full body lotion for most of the year. 

But for something a bit longer lasting, more moisturizing, and still neutral scented, Benamôr Gordissimo’s hand cream does wonders. Plus the metal tube form factor is cool and very satisfying to use. 

Benamôr Gordissimo Nutritive Hand Cream | $18

Bevel Body Lotion 

#2: Use a richer, daily moisturizer

Winter skin often needs a richer, daily moisturizer to help nourish, hydrate and protect the skin from uncomfortable dryness or cracking.

The best time to moisturize is after showering or bathing, while skin is still warm and damp to help increase absorption and lock in moisture.

While we love our Aveeno, we found during the winter it required a lot more application due to having more water content. 

Made without harsh drying chemicals, we opted for Bevel’s daily body lotion to keep our body moisturized all winter long. 

Bevel All-Day Moisture Body Lotion | $10


Bevel Hand Soap

#3: Use lukewarm water and hydrating soap

We love steaming hot water showers, especially in winter when it's cold out. However, with the lack of humidity in the winter, the hot water strips away natural oils and thus more easily dries out your skin.

Instead, crank the heat down and aim for lukewarm water to help prevent skin dryness.

Additionally, aim to use a gentle, hydrating soap. 

Dry winter skin conditions are often exacerbated by harsh detergent soaps that contain fragrance oils and synthetic chemicals that wash off natural skin-protecting oils.

Bevel Exfoliating Bar Soap 2-pack | $12

Men’s Winter 2020 Fashion & Beyond

Our comprehensive men's casual winter fashion guide for 2020 is packed with different fabrics, colors, and textures that are on our list of must-haves to be styling while dashing through the snow and a season spent more time indoors. 

Did we miss anything? Any favorites or recommendations? 

Leave a comment below or email us so we can improve and update this guide accordingly.

And last, but not least, here is a huge inspiration album we put together: 

Mens Winter Casual Outfits

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