Men’s Winter fashion is something that can go either way. Maybe you’ll find that you ace it and look fantastic in a winter outfit that has lots of interesting layers and makes you look classy and savvy. But maybe you’ll find you’re more likely to look like a stuffed turkey, constantly struggling with too many layers, and covered in sweat!
Related: Men’s 24-Piece Capsule Wardrobe
Determining which comes down partly to choosing the best men’s winter fashion essentials. With that in mind, read on and we’ll explore some of the items that every guy should have in his wardrobe.
If the temperatures aren’t quite cold enough yet for winter wear, check our Men’s Fall Fashion Essentials Guide.
Winter Outfit Fabrics
Cotton is one of the most widely used fabrics in clothing and results in high quality, beautiful clothing, that feels soft and keeps its appearance for a long time.
There are lots of different kinds of cotton to work with. Corduroy was big in the 70s and is making something of a comeback right now. We’re not sure we’re ready to recommend corduroy pants or jackets… but they’re great for a shirt.
Melange is cotton that combines two different colors and has a softer feel that’s great for shirts.
Flannel is a material that looks great on a checked shirt. It’s a soft, woven fabric that was initially made from carded wool or worsted yarn. Today, it’s usually wool, cotton, or synthetic fiber. Either way, winter is a great time to bring it out and flannel shirts have been enjoying a surge in popularity for the past several years now!
Wool is highly insulating and has a very warm and welcoming look to it. Women love a man wearing a wool jumper who looks ready to hug, and this can also be a great way to emphasize your masculinity by the way it contrasts a face of stubble or torn jeans.
There are lots of different types of wool, ranging from lambswool – which has a more rugged texture, to mohair, flannel, merino, tweed, and cashmere. These all say very different things. While tweed has a learned and studious aesthetic that goes great with a scarf and long overcoat, cashmere is beautifully soft and flat to the touch and works great in a sweater over the top of an Oxford shirt.
Knitted wool jumpers are also ideal for winter and particularly when you’re relaxing on the sofa.
Leather is made from hiding and is extremely tough and long-lasting. EVERY man needs a leather jacket, and winter is the perfect time to bring this out. This is also a great time to get yourself a suede leather jacket with a wool lining, which will keep you nice and warm and has echoes of the “lumbar-sexual” movement.
Men’s Winter Fashion Jackets
One of the great things about winter is that it’s a time you get to bust out your jackets. A jacket lets you add an entire layer on top of whatever you’re wearing, instantly making the overall outfit significantly more interesting and versatile.
A peacoat is an overcoat that is usually navy and made from heavy wool. A long coat such as a pea coat is a men’s winter fashion essential, owing to the fact that you need something a little longer to wear over a suit!
Peacoats look great with a scarf underneath tied in a loose noose style and can be worn to formal occasions thanks in part to the smart, double-breasted front.
For our purposes, a parka is a hooded longer winter jacker. The hood can also come with a fur fringe for extra warmth and styling. A parka is great for deep winter days where the temperatures drop well below freezing. Parkas are warmer than many other types of jacket and look great in navy, black, or grey.
A technical jacket is a “weather resistant” jacket, usually made from enhanced synthetic materials that can stand up to harsh conditions. While repelling sweat and moisture during extreme activities like hiking and skiing. This makes the technical jacket a popular choice for those wanting to do a bit of trekking, but it also makes it a smart looking jacket for every-day casual wear. It looks good weather you’re doing a spot of shopping or heading out to the gym.
Note that there is a range of technical jackets that are becoming increasingly popular lately. This is part of the “tech wear” trend that is quickly growing to rival the recent “athleisure” wear. As with the technical jacket, the idea behind tech wear is that you are wearing outfits where every detail serves some kind of purpose.
These jackets are lighter than technical jackets and only a little thicker than a technical shirt. They tend to come in khakis, tans, and dark shades of green and feature plenty of pockets. They are practical and make a great everyday jacket for quick outings. One thing to keep in mind. If you temps drop below 36-degrees I’d look for a more substantial winter jacket for your outfit.
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
Merino V-Neck and Crewneck 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. The crewneck sweaters are great for casual days over a t-shirt. Whereas the v-neck is perfect for layering with an oxford and a tie for a more business casual outfit. So you get the most out of your winter outfits, I would start with black, grey, and navy which should go with almost everything in your winter wardrobe.
Related: Best Men’s V-Neck Sweaters
The Oxford shirt is your plain, standard button-down that you can wear to the office. Or roll-up the sleeves and wear with a pair of chinos. Details that usually identify an Oxford shirt is a button-down collar and long sleeves. It is not just a men’s winter fashion essential, though you will find that you probably feel comfier wearing this kind of shirt when it is a little colder out. If you are going to wear in spring and summer with shorts just make sure you roll up those sleeves.
A Henley is a tee with long or short sleeves and normally a low v-neck with buttons. This is a more structured alternative to the tee, which looks great when form-fitting on a more muscled physique. Henleys are also warmer than your typical tees, which makes them a great choice for wearing during the winter. That said, this is also their main downfall, as it can be tricky to layer on top of the Henley.
These look particularly great in light grey, white, khaki, or navy.
Flannel shirts have been popular among men for a while now. They’re usually worn as an overshirt with a white tee over the top and will sport checked patterns and deep red and green color schemes. Although, I personally like to switch things up and get my flannels in a solid like the example above from H&M.
This is the shirt that a guy wears who is willing to brave the elements and still get work done! The kind of guy who’ll go and chop down that Christmas tree and drag it into the house. It’s a great look, and especially if you’re rocking a hipster-chic with a beard and all the trimmings (yes, that’s a pun).
Sweatshirts and Hoodies
Sweatshirts and hoodies are men’s winter fashion essentials and another example of an item that is essential all year round.
Starting with hoodies, these are ideal for hiding from the wind and staying warm, while at the same time dressing down. Of course, a winter hoodie will generally be made from a warmer fabric and may even be fleece lined. They can look great underneath a jacket of some sort, or worn indoors when kicking back.
For a more formal look, I’d go with a nice Crewneck Sweatshirts. You can just go with a t-shirt underneath or pair with an Oxford button-down to dress it up for casual Fridays at work. Steer away from thin low-quality materials that’ll pill overtime. Aim for something heavier and higher quality like the offerings for Sunspel.
Men’s Winter Fashion Pants
It’s common for guys to think hard about their upper body when it comes to men’s winter fashion essentials, but to forget all about their lower half. Thing is, legs get cold too! And you’ll need to rethink your wardrobe if you’re going to select items that will go with the rest of your new ensemble. Those linen pants just aren’t going to cut it now!
And with that in mind, what types of pants should you look for in winter? Let’s go over them.
Finally! The time of year where denim jeans actually make sense and are somewhat comfy. You’ve probably been battling them all summer, but now you can embrace the denim and look great doing so. Get yourself some regular fit jeans with a dark wash to dress your outfit up with a smart shirt, and some distressed, lighter wash jeans for staying casual.
The wool pant is an item that more men should invest in. This is your equivalent of denim or chinos during the winter – it’s a little bolder and more interesting than a standard formal pant, and goes great with a more contemporary get-up. In particular, these look great with a plain white Oxford shirt, and maybe a pair of nice brogues. Because wool pants use a thicker material make sure to get them fitted so you don’t look like a bag of potatoes.
Of course, there is always the option of bringing out the corduroys. This is the perfect example of a “high risk, high reward” gambit. Only for the confident!
That said, you can still wear chinos in winter and in fact they’re actually pretty warm. That makes them men’s winter fashion essentials too. Generally, go for lighter colors with your chinos as compared with wool pants, or neutral colors that will match a great set of brogues.
Men’s Winter Fashion Boots and Shoes
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. Made primarily 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. Just slip them on and you don’t have to worry about rain, snow, or ice.
Related: Best Winter Shoes for Men
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 throw these bad boys on instead of sneakers and you don’t have to worry about losing your footing.
Winter is not just about looking great in overcoats and scarves, it’s also about relaxing at home with the family in a thick sweater, nursing a mug of hot cocoa. For that other side of winter, you’ll want to head out in some darker color sneakers. They go great with jeans, and they perfectly complement a comfortable outfit choice. Our favorite colors and dark navy, grey, and black. If conditions are dry you can also break out those white kicks for one last hurrah.
Leather Boots for Men’s Winter Fashion
Whether it’s a Chelsea boot, a set of suede brogues, or chukkas, winter is THE time to crack out the boots.
Heck, even hiking boots/walking boots belong in your men’s winter fashion essentials list. If you plan on heading off the beaten track and enjoying that fresh air, then you’re going to need some protection from those icy puddles and some grip for the slippery surfaces.
This is a broad category, but you will also need a set of dress shoes (or a few) for those more formal occasions. These should go with your wool pants, as well as your suit. A great choice is to go with a derby brogue. These have heavier patterning which is a good fit for the heavier materials you’ll wear during winter.
You can also use a monk strap boot if you want a little more ankle support and warming during the colder months.
Men’s Winter Fashion Accessories
We’ll finish up with winter accessories: this is certainly a time of year when we can bring out a lot of the most interesting and exciting featured!
Here are a few things you’ll need to complete the look:
- Wool socks – These will keep your feet warm and match your heavier-set pants and shoes.
- Sunglasses – Especially in the winter! In the winter is low on the horizon and you will get a lot of direct blinding sunlight especially in the morning and early evening hours. This glare is particularly bad in snowy climates where the sun will also 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.