Here’s What Stylish Men Wear in Winter

For a lot of men, fashion consists of just throwing on jeans and a t-shirt. In the winter, these men might wear a hoodie over their t-shirt and layer a puffer jacket over that. While there’s nothing wrong with t-shirts, puffer jackets, and hoodies, there’s a lot more that goes into looking sharp and fashionable in the winter.

If you’re a man who wants to look stylish in winter, you need to pay some attention to clothing trends, but you also need to be willing to switch things up and leave your comfort zone. Let’s take a look at some strategies you can use to look more stylish this winter.

Switch Up Your Outer Layers

You’re probably accustomed to wearing your formal overcoat to the office and donning your puffer jacket on evenings and weekends. But, if you think about it, you don’t really need to wear your formal overcoat to the office – you’re going to take it off the minute you get there, anyway. 

Spice up your winter look by switching up your outer layers. Wear your puffer jacket or parka over your suit to the office. It’ll add some new energy and life to your look this season. If you really want to be bold with your look, grab a non-traditional outer layer, like a cape or poncho, or even a blanket scarf.

Warm Up Your Inner Layers

Layering can be very important for staying warm in the winter, especially if you’re going to be spending some time outside. But you don’t want to look like a stuffed sausage with a lot of invisible layers. And you do want to be able to stay warm if you have to remove an outer layer.

A warm, chunky inner layer can ease your dependence on thick outer layers. A thick sweater over thermal underwear can keep you warm enough that you only need a light jacket or no jacket at all over top. A thin but warm inner layer, like a merino sweater, can keep your profile slim. If you’re layering up, make sure each layer is visible from the outside to avoid the sausage effect.

Mix Formal and Casual Pieces

Add some interest to your look by mixing formal and casual pieces in the same outfit. Grab one of your favorite hoodies for men to wear over fitted slacks and dress shoes, or wear jeans with a button-down, vest, and jacket. Offset your casual Friday staples with more refined, Monday morning pieces for a laid-back, but still professional, appearance.

Wear Your Boots

Boots are a winter footwear staple, and they present a unique opportunity to play around and get creative with your footwear. There are just so many styles of boots to choose from, and you can use the excuse of the weather to wear just about any pair of boots with any outfit. Grab a pair of Chelsea boots, combat boots, or shoe-boots – whatever strikes your fancy, as long as it has good tread and a warm lining.

Wear Your Sunglasses

Yes, you do need sunglasses in winter. They can keep dust and wind out of your eyes, but they also protect your vision from the sun’s glare bouncing up off the snow. Bright winter days can literally be blinding.

Grab tortoiseshell or neutral colored frames in keeping with the season. Sunglasses will add some mystique to your look, and they’re perfect for those days when you’re tired, hungover, sick, or just in a bad mood and want to keep your distance.


This winter, when you’re getting dressed, put down your most formal accessory and replace it with something more casual. Usually carry a briefcase in the summer? Grab a canvas satchel for the winter instead. Replace your monk-strap shoes with combat boots, or your Oxford button-down with a flannel. Don’t be afraid to leave your comfort zone – it can only help with the look.

Of course, as your mother may well remind you, you also need winter accessories to keep warm. Sport a beanie, long scarf, and gloves or mittens. Winter knits in neutral colors and classic motifs will add some traditional flavor to a contemporary outfit, and keep you comfortable, too.

If you’re a man looking to dress more stylishly this winter, it’s time to get out of your comfort zone. Mix and match your formal and casual pieces, and don’t forget to dress for the weather. You may be surprised at how sharp you can look while still staying warm and cozy.




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It's a little lonely being one of the two female writers here, but I do my best! You'll find me covering everything from relationships to the newest gadget I'm excited about.

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