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Men’s fashion: These casual styles for men will keep you looking cool while staying warm

Winter weather fashion trends that will keep you stylish

Man in winter sweater and beanie
Image used with permission by copyright holder

It’s that time of year. Summer is a distant memory, and when you get up in the morning, you notice frost on the window. Yup, winter is coming. As winter temperatures drop and snowstorms blow in and out, you may find yourself wanting to stay in as much as possible. However, if you feel the need to leave your warm haven and brave the snow and ice, you can do so while staying warm and trendy with some of our favorite men’s fashion trends.

While style trends come and go, there are some men’s casual winter fashion items that never go out of style. If you don’t have some or all of these items, pick them up ASAP to make yourself the most stylish and warmest guy in your group.

Man in a plaid shirt and cardigan


Mister Rogers may have brought these mainstays to the forefront of men’s fashion, but they’ve become a staple of masculine style. They come in all colors and fabrics, ranging from thin fall sweaters to thick and warm winter garments. There are some great ways to wear these and look better than ever.

If you want to wear a cardigan to the office, you can swap out your suit or sports coat with a stylish cardigan and a shirt and tie. If you’re going to wear one in a more casual way, double up and wear a thicker cardigan over a crew neck. Or you can opt for a lighter-weight cardigan and wear it over a T-shirt or henley around the house.

Man in turtleneck and jacket
Andrea Piacquadio / Pexels


Whether your first time seeing a turtleneck was on the cover of The Beatles album “With the Beatles” or watching a presentation given by Steve Jobs to release Apple’s new tech, you’ve likely seen them everywhere since that first time. While they may qualify as a sweater, they look great underneath other layers, making them more of a basic than a final outer layer.

Turtleneck sweaters look great on their own, but if you want to punch them up for a date, you can layer a sports coat over them. You can also layer them under a bomber jacket for a more casual look, or under a flannel for an outdoor ensemble.

Man in a black turtle neck, black and tan shearling jacket, and gray knit pants
Image used with permission by copyright holder


Our next stop on the men’s winter fashion tour brings us to a classic look that will keep you looking good while you’re staying warm. Worn by everyone from western ranch hands to mountain climbing sherpas, shearling-lined coats offer some of the best protection from the winter elements that you can buy. Taken from the sheepskin of a young lamb, the wool is warm, soft, and stylish as hell.

Obviously, this is an outer layer. Wearing a shearling-lined coat is great for when you’re working, sure, but don’t think this coat can’t punch up any casual outfit to make it more than a basic look, making you the life of the gathering.

Man in a tweed suit, standing in a field
Image used with permission by copyright holder


Tweed isn’t only for old college professors. It’s a thick and patterned fabric used in jackets, suits, and accessories, such as hats and bags. While the origins reach all the way back to the Irish and Scottish highlands in the 19th century, tweed has become a staple in every country and at every level of fashion.

Now is the time to switch out your lighter fabrics that breathe well in the warmer months with a heavier material like tweed. Since this is about casual style, we’re not here to discuss the three-piece tweed suit, but there are fewer stylish garments than tweed pants when you’re looking for a way to stay warm and look good. While you’re at it, go full British and grab yourself a tweed flat cap.

L.L. Bean Tumbled-Leather Bean Boots
L.L. Bean

Waterproof boots

You can have all the warm, stylish clothes you want, but you’ll never be truly comfortable in the winter if your feet are cold and wet. That’s why a good pair of waterproof insulated boots should be a part of your casual winter fashion wardrobe. One of the more popular designs is the classic Bean Boots from L.L. Bean. Originally called the Maine Hunting Shoes, these durable boots come with a waterproof rubber bottom and a soft leather top for comfort. The boots, which are still hand-stitched in Maine, have come a long way in their over 100 years of existence, going from the woods to being part of a casual winter wardrobe for a night out in the city.

Man in a flannel shirt driving a truck
Image used with permission by copyright holder


It doesn’t matter if you have a beard or an axe; flannel is for you. There are very few fabrics or looks that give you a more masculine aura than a flannel shirt. And while it’s made to be a shirt, it can also easily act as a light jacket if the weather is just slightly too cool for a shirt but not quite cold enough for a coat.

Now that you have the fashion trends for a casual winter in style, you have all you need to look better than anyone in your group for the next few months.

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Mark McKee
Mark is a full-time freelance writer and men's coach. He spent time as a style consultant and bespoke suit salesman before…
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