10 Men's Style Tips To Help You Dress Better In Winter (2025)

There’s a common misconception that to dress warmly, one must abandon sartorial grace in favour of unbridled practicality. Big bulky parka, bobble hat, insulated snow boots. But do you really have to dress like Luke Skywalker on Hoth to survive the winter? No. We believe there’s a knack to balancing style and comfort for more city-appropriate cold-weather ‘fits. It’s just a case of learning a few new tricks.

From the types of cloth you choose to clad yourself to the sort of rubber stitched to the soles of your shoes – these seemingly small details are the difference between faltering and flourishing in less-than-tropical temperatures. In other words, warmth and style don’t have to be mutually exclusive when you unlock the secrets of dressing smart in the cold.

Keen to learn more and take your deep winter looks from zero to hero? Here, we count down our carefully honed top tips for navigating the iciest days of the year without sacrificing style. From pro-level layering to harnessing the power of merino, here’s what you need to know.

Layers, Layers, Layers

Winter in the city means going from arctic cold to heated indoor environments in the blink of an eye. The only way to dress for these dramatic temperature shifts is to layer, and layer well. This will allow you to modulate your temperature by adding or removing layers depending on the environment. It’ll also keep you warmer when you do go outdoors, as multiple layers of fabric trap body heat more effectively.

You should be aiming for at least three or four layers. A base layer, like a T-shirt or a Merino long sleeve; a knit of some sort, something fine or chunky depending on the temperature; possibly a light jacket of some description; then a nice comfortable coat to top it all off.

The Right Kind Of Big Coat

Speaking of which, picking the right winter coat might just be the most important style move you’ll make all year. Your outer layer has a unique power to make or break any outfit, so finding something that complements many different looks is a must.

It’s a common mistake to choosethe biggest, warmest parkapossible without considering how it will look with the rest of your wardrobe. Instead, we suggesta classic wool overcoat.

A heavy, tailored topcoat with slouchy raglan sleeves and a loose fit is smart enough to wear with tailoring while remaining relaxed enough to pair with jeans and sneakers. It’s an extremely versatile outerwear style and does a remarkable job of blocking the cold, wind and even shrugging off showers.

Tied Up In Knits

If T-shirts are the backbone of the summer wardrobe, the same could be said of knitwear in the winter. Knits are the foundation of your cold-weather looks. They trap the heat and work with your outerwear to seal out the cold, while the rich texture holds dye beautifully, making them the perfect vehicles for bringing a pop of colour to the table.

There are all sorts of knits to consider, but to get the ball rolling we suggest arming yourself with a cashmere crew neck and a thicker textured cardigan.

You Gotta Have Sole

You can get everything else right, but even the best-dressed guy in the city will struggle to look good slipping and sliding like Bambi on ice. This is why choosing the right footwear for the conditions pays dividends.

Forget those Derby shoes and their flat leather soles. You need something grippier and more winter-appropriate. Thankfully, plenty of the best shoe brands offer a variety of classic styles with lugged ‘commando’ soles that make it easier to keep your feet planted on wet or icy ground.

Big Boy Jeans

Unless you’re a seasoned denim head, you might not have paid attention to denim weights and their impact. Heavier denim is not only tougher and more durable, but it’s also warmer than its lightweight and mid-weight counterparts. This is because it is much thicker, making it better suited for wear on the coldest days of the year.

Spend the money ona good pair of raw selvedge jeans and enjoy the process of them fading and conforming to your body over time.

Cashmere Rules Everything Around Me

Yes, it’s expensive, but cashmere is one of the best materials for winter wear if you can afford it. It’s a fantastic insulator, impossibly soft, and great for adding a touch of visual texture to outfits.

Can’t stretch to something as expensive as a pure cashmere sweater? Fear not, because one of the best ways to get the most out of cashmere is to buy the cheaper options: the accessories. A cashmere beanie or scarf is something you can wear again and again with all sorts of outfits, and it’s generally a lot more affordable than buying a full jumper or cardigan made of the same stuff.

Keep It Muted

A well-placed pop of colour here or there can be a powerful tool, but there’s something to be said for keeping things toned down and muted overall.

This is an easy way to ensure a more grown-up and sophisticated look, and it means you can mix and match garments more freely without worrying about clashing colours.

All About That Base

On the coldest days, it’s not your outerwear that’s the most important layer; it’s what you choose to wear next to your skin. Your base layer is your first line of defence against the cold. Get it right and the rest will follow.

Merino is a marvellous material in this department. It traps heat effectively, is quick-drying, and has natural moisture-wicking properties to keep you comfortable, warm and dry in various conditions. Choose one that fits close to the skin and no one has to know you’re wearing it at all.

Focus On Fabric

Merino, cashmere, fleece – winter style isn’t just about knowing what looks good; it’s about understanding how fabrics act and whether they’ll keep you warm.

Start with that as a foundation and then think about the visual aspect and how different textures look next to each other. When you do that, you’ll unlock a whole new level in winter style.

Socks Appeal

If you’re keeping your outfit muted, socks become one of the best places to demonstrate personal flair. Something with a bit of colour, texture, or both will do the trick.

Think flecked knits, textured patterns, and thick knits. Check out brands like Anonymous Ism and Ro To To for some of the best.