Winter Outfits for Men: How to Stay Warm and Stylish

Winter style doesn't have to mean choosing between looking good and staying warm. Here's how to nail both.

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A man wears a quilted jacket, scarf and jeans, carrying a tote bag

Meet your cold-weather basics

Winter dressing brings its own unique issues. Dressing for warmth, without looking like a polar explorer, being able to deal with gale force winds and teaming rain while still looking sharp. The solution? Layer smart, choose quality fabrics and invest in versatile pieces that will work hard all season long.

The trick to great men’s winter outfit ideas is balance. Think lightweight layers that insulate – merino, cashmere, wool – paired with outerwear that stands up to the elements. A soft cashmere jumper instantly elevates any winter look, while a well-cut wool coat or quilted jacket adds warmth without sacrificing style. Don't forget the finishing touches – a wool scarf and leather gloves complete the look.

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A man wears a puffer coat with a crew neck jumper, jogging bottoms and trainers

Casual winter outfits for men

When the weekend calls for easy, comfortable dressing, the best casual winter outfits for men combine effortless layers with pieces that work hard in cold weather.

Start with joggers (these fleece-lined ones are particularly cosy) or well-cut jeans, then add knitwear. Think classic crew necks, half-zip styles or lambswool jumpers you can wear on repeat. If you need an extra layer of warmth, add a thermal top underneath your knitwear.

Outer layers make all the difference on crisp winter days. A fleece jacket adds instant warmth for dog walks or quick errands, while a lightweight gilet is ideal for days when you’re constantly on the move. For something a little sharper, a wool-blend Harrington or funnel-neck jacket offers comfort with a smarter edge, an easy upgrade when you want your off-duty look to feel more considered. And when the temperature really drops, a puffer jacket is your reliable go-to, delivering insulated warmth without weighing you down.

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A man wears a pale wool blazer over a white shirt and crew neck jumper, matching it with pinstripe trousers. He's sat on a stool against a pale background

Smart winter outfits for men

Cold-weather dressing doesn’t have to complicate your working day. The best smart winter outfits for men balance sharp tailoring with layers that genuinely keep you warm. Start with a crisp shirt, then add smart knitwear – a cashmere V-neck or fine-gauge crew neck works perfectly under a blazer without adding too much bulk. This simple combination works for most winter work outfits for men, whether your office dress code leans towards formal or relaxed.

When it comes to trousers, tailored wool styles or smart chinos offer both warmth and structure. Pair them with a wool blazer for a polished take on smart casual winter outfits for men, ideal for client meetings, commuting or days when you want to look put-together with minimal effort.

On the coldest days, a smart wool coat completes formal winter outfits for men with a polished finish. If you’re wearing it over a suit, make sure it has enough room to sit comfortably over your tailoring.

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A man wears a brown jumper, dark jeans and brown chelsea boots

The best men’s boots and shoes for winter

When the temperature drops, the best men's boots for winter combine durability with everyday style. Chelsea boots are a go-to: clean, versatile and easy to wear with everything from dark denim to smart-casual trousers.

If you need something for more active pursuits, walking boots are a great choice. The soles are non-slip and the waterproof outer protects you from rain, mud and winter slush.

When your winter looks need polish, Derby shoes remain some of the best men's shoes for winter, thanks to the timeless design. For a more smart-casual feel, chukka boots offer comfort and structure, ideal for weekend plans or laid-back office days.

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Published 11.28.2025