Men’s Winter Fashion is all about layering. Winter is one of the best seasons for getting the most out of your wardrobe. You’ll get full use from your coats, and jackets as well as sweaters, and cardigans.
In this article, we’ll explore the most essential items for a men’s winter wardrobe. Providing everything you need including items for those milder days.
Men’s Winter Fashion FAQ
Before we get started, let’s answer some of the most common questions about a winter wardrobe.
Think of this guide as an addendum to our Men’s 24-Piece Capsule Wardrobe Guide. In that article, we provide the core items a thoughtful wardrobe should contain. In this guide, we add on all the pieces and accessories needed for those colder months.
Like our capsule wardrobe, I want to keep coloring as basic as possible. If you’re building your wardrobe start with blacks and greys. Then add in blues and beiges.
If you’re not dealing with a ton of exertion or damp conditions any material can work. But the most common is wool.
There’re lots of different types of wool. These include lambswool, which has a rugged texture. To mohair, flannel, merino, tweed, and cashmere. These all say very different things style-wise. Tweed has a learned and studious aesthetic that goes great with a scarf and long overcoat. Cashmere is soft to the touch and works great in a sweater layered with an Oxford shirt. Although cashmere is a luxury material, prices have come down recently.
If you’re thinking about winter fashion, you’re thinking about coats and boots. Some of our favorite coat and jacket brands include The North Face, Moncler, and Canada Goose. As far as boots you can’t go wrong with Sorel, Kamik, Columbia or Baffin.
Men’s Winter Coats & Jackets
One of the great things about winter is that it’s a time you get to bust out your coats & jackets. A good winter coat not only keeps you warm the layering allows you to increase your wardrobe options.
Wool Overcoat
A wool overcoat is one of my favorite options. A long overcoat is an absolute men’s winter fashion essential. You can wear it with anything in this wardrobe. Layer it over a suit or even your favorite hoodie. A good overcoat is a must-have in any winter wardrobe.
Left to Right: Feathered Friends Rock Ice Parka, North Face Men’s Himalayan Parka & Canada Goose Men’s Expedition Parka
Quilted Winter Coat
If it’s winter, you’re going to need a solid winter coat or jacket. Especially with those temperatures start dipping below the freezing mark.
My focus is usually on style first and warmth second. But when you’re in New York or Philadelphia, in the middle of winter, and the winds are blowing, you stop giving two f#@ks about style.
For our purposes, anything with a fill power rating between 600-800 will do the trick. You should also consider a hooded coat or something with a removable hood. As far as length goes I’ll leave that up to you.
For extra information check out our winter coat buying guide
(Canada Goose Hybridge Base $650)
Down Vest
The one outerwear item I wear more than any other has to be my down vest. I wear it daily with my hoodie, layered with an overcoat, or even under a blazer. One of the most versatile items in my wardrobe. The one I wear from Uniqlo is lightweight and packable, so it’s easy to take on weekend trips.
Men’s Winter Style Shirts and Sweaters
Left to Right: J. Crew Merino Wool Crewneck Men’s Sweater, Asket Merino Wool Men’s Sweater, COS Merino Wool Men’s Jumper, John Smedley Merino Wool V-Neck Men’s Sweater, H&M Merino Wool V-Neck Men’s Sweater
Wool Merino Sweaters
If you’re going to wear a sweater this winter, you can’t go wrong with either a Merino wool crewneck or a v-neck. Crewneck sweaters are great for casual days over a t-shirt. Whereas the v-neck sweater is perfect for layering with an oxford and a tie. This results in a nice business casual outfit. So you get the most out of your winter outfits, I would start with a black crewneck, add in a cardigan and then a v-neck.
Left to Right: Asket The Oxford Shirt, J. Crew American Pima Cotton Oxford, Farnol Everyday Oxford Shirt
Oxford Shirt
The Oxford shirt is a casual button-down you can wear to the office. Or roll up the sleeves and wear with a pair of chinos. Most oxfords will have a button-down collar. You can layer this with any of the sweaters or even a sweatshirt.
Plain T-Shirts
Yes, even in winter you’ll need some nice plain t-shirts. You’ll be layering these bad boys with sweaters, sweatshirts, and your button-downs. And for those quick trips to the store, you can throw an overcoat or a quilted vest over your t-shirt. Especially on those milder days.
Wool Flannel Shirt
Now I know what you’re thinking. Most of us think of flannel with think of bright bold patterns. But for this wardrobe, I’m thinking of a plain wool shirt made from a fine wool or wool blend.
Layer a wool flannel over a t-shirt, leave it untucked, and you’re good to go. Uniqlo and H&M make great affordable flannel shirts. If you’re looking for the Cadillac for wool blend shirts, check out the offering from Wardrobe.NYC.
Left to Right: Sunspel Loopback Sweatshirt, H&M Hooded Sweatshirt, Handvaerk Varsity Sweatshirt, Asket The Zip Hoodie, NWKC 003 Pullover Hoodie
Sweatshirts and Hoodies
I wear sweatshirts and hoodies year-round, but they come into their element in the winter. During these cooler months, sweatshirts and hoodies are worn daily. My philosophy is if I touch it every day I’m going to want quality. This includes clothing, appliances, tech, rides, whatever. I want to know it’ll last and continue to hold its shape over the years. I usually buy my sweatshirts from stores like the British Co. Sunspel. Their sweatshirts run about $145 while their hoodies go for $195. They do have seasonal sales which help a lot.
Denim Shirts
Another great shirt for a men’s winter wardrobe is the denim shirt. If done right you can wear with jeans, chinos, or wool pants. When wearing jeans I like to go dark on the bottom and lighter on top. Black jeans with a blue dark wash on top. You can also pair a blue dark wash denim shirt with any color chino. Olive, beige, dark blue, or black.
Overshirts
As the name indicates, an overshirt fits in the middle ground between a light jacket and a heavy shirt. I like to treat them as more of a heavy shirt. Perfect for layering in the cooler seasons. Overshirts usually feature chest and side pockets. And can have buttons or zippered fronts. The materials used are cotton twill and wool. If you’re in the market, A Days March has great overshirt offerings and affordable prices.
Men’s Winter Fashion Pants
The four must-haves when it comes to winter pants are denim, wool pants, and chinos. You also need sweat pants for your workouts and leisurewear. All these guys will keep you nice and toasty in some of the coolest temperatures.
Left to Right: Mott and Bow Men’s Jeans, J. Crew 484 fit Men’s Jeans, Levis 511 Slim Fit Men’s Jeans
Denim Jeans
Finally! The time of year where denim jeans actually make sense and are somewhat comfortable. You’ve been battling them all summer, but now you can embrace the denim and look great doing so. Get yourself some slim-fit jeans in a dark wash and you can’t go wrong.
Left to Right: COS Slim Wool Trousers, Sunspel Wool Cashmere Flannel Drawstring Trouser, Samsoe-Laurent-Wool-Pants-6568
Wool Pants
For the longest time, I never wore wool pants unless I was throwing on a suit. They have definitely become more of a staple in my wardrobe. Not only do I include tailored wool pants in my wardrobe, but also casual drawstring pants. I wear these with casual items like hoodies and merino crewneck sweaters.
Left to Right: Bonobos Chinos, J. Crew 484 Slim Fit Men’s Chinos, Uniqlo Slim Fit Flat Front Chinos
Chinos
A great pair of chinos are a must for a complete winter wardrobe. I wear chinos at any time of the year, but they also work great in the winter. During the winter I usually go with dark colors like olive, dark blue, and black.
Sweat Pants & Joggers
If you’re anything like me, once you hit the weekend being comfortable is a priority. Joggers and sweatpants paired with a great hoodie or sweatshirt are about as good as it gets. You can also wear a nice jogger with a button-down shirt and a merino sweater for a great out-of-the-box look.
Men’s Winter Fashion Boots and Shoes
Left to Right: L.L. Bean Men’s Storm Chaser Slip-On Winter Shoes, Salomon Men’s Snowclog Winter Shoe
Men’s Winter Shoes
The shoes in this category aren’t very stylish. But if you’re in cold, sloppy conditions you’ll definitely what a pair of good winter shoes. Made for walking on ice and the slopes they have deep lugs in the sole for some great traction. I keep a pair of these shoes by the door I use most in the winter. Slip them on and you don’t have to worry about rain, snow, or ice.
Great for those quick trips to the store or shoveling the driveway when the snow depth doesn’t call for a full boot. My two favorite bands are the L.L. Bean Storm Chase, and the Salomon Snowclog.
Bonus use for these shoes: If you’re cutting wet grass or have hills in your yard use these instead of sneakers. You’ll never worry about losing your footing again.
Left to Right: New Balance M996 Casual Men’s Sneakers, Nike Kill Shot 2 Men’s Sneakers, Maison Margiela 22 Classic Replica Sneaker, New Balance x J. Crew 791 Leather Sneaker
Sneakers (Casual & Luxury)
For that other side of winter, you’ll want to head out in some darker color sneakers. They go great with jeans, and they complement a comfortable outfit choice. Our favorite colors and dark navy, grey, and black. My favorite brands are New Balance, Oliver Cabell, Common Projects, and Maison Margiela.
If conditions are dry you can also break out those luxury white kicks for one last hurrah. Whether you have a pair of Oliver Cabells or Common Projects, go ahead and sport them on those dryer days. Make sure you have a shoe cleaner to keep those guys crispy white.
Left to Right: Red Wing Heritage Men’s Moc Toe Boot, J. Crew Kenton Leather Pacer Boots, Alden X J. Crew 405 Indy Boots, Dr. Martens Cabrillo Men’s Leather Boots
Men’s Leather Boots
Whether it’s a Chelsea boot from Grensen. A leather dress boot from Alden, a leather workboot from Redwing. Or a pair of chukkas for Clark. Winter is the time to crack out the leather boots.
Some boots I’ve been working into the rotation more lately are my leather Chelsea’s. I wear these with any of the pants I’ve listed in this wardrobe. Including jeans, chinos, and my wool pants.
Left to Right: Charles Tyrwhitt Oxford Dress Shoe, Trickers Woodstock Derby Dress Shoes, Allen Edmonds MacNeil Dress Wingtip Blucher Dress Shoe
Derby Shoes
This is a broad category, but you’ll also need a set of dress shoes (or a few) for those more formal occasions. The great thing about Derby’s is you can wear them with a suit or throw them on with jeans or chinos. They’re a broader less formal shoe than Oxfords. And go great with the heavier materials worn during winter.
Men’s Winter Fashion Accessories
We’ll finish up with winter accessories. this is a time of year when we can bring out a lot of the most interesting and exciting features! Here are a few things you’ll need to complete the look:
Left to Right: Tudor Heritage Black Bay Watch, Warby Parker Aviator Sunglasses, L.L. Bean Wool Socks, Everlane Ribbed Cashmere Beanie, Barbour Leather Utility Glove, Barbour Lambs Wool Scarf
- Wool socks – These will keep your feet warm and match your heavier-set pants and shoes.
- Sunglasses – Especially in the winter! In the winter the sun is low on the horizon. Causing direct blinding sunlight especially in the morning and early evening hours. This glare is particularly bad in snowy climates where the sun will reflect from the ground.
- Scarves – Add a scarf to any overcoat to instantly look studious and smarter
- Watches – Watches are great fun in winter. The key is to ensure you leave just enough wrist showing to actually have them on display. But the fact that you’re wearing more, means you can also get a little more experimental with timepieces.
- Beanies – Lots of hats work well in winter, but we’re going with beanies. They’re versatile, easy to carry, and they can completely change your look in seconds. They’re perfect for dressing down an outfit when you get out of work.
- Gloves – Finally, get yourself some high-quality leather gloves that you can actually do things in. They’ll keep your hands nice and soft and they can put the finishing touches on an outfit.
