8 Winter-Ready Trouser Styles Every Man Should Own

When the cold weather sets in, the natural response of sartorially minded men is to start perusing heavy outerwear and knitwear and thinking about layering. Most of the time (if not always) this attention is focused on wrapping the upper body up. But when the mercury really dips, you’ll be losing a lot of heat through your legs too.

So, what’s the solution? You can’t wrap your legs up in layer upon layer like you would your torso, so how can you keep them from getting too cold?

Your best bet is to get smart with your legwear choices, giving more thought to things like material and insulation. In other words, you need some winter-specific trousers to get your pins through the cold months in comfort.

If you’re used to just throwing the same pair of jeans or chinos on most days, you might not be aware of the number of winter-friendly options available to you. Rest assured, there are plenty. And to help you find the ones that are best suited to your style and local climate, we’ve rounded up some of the key styles to consider.

So from heavyweight denim to all-out insulated snow pants, here are the winter trousers every man should know.

Cords

Corduroy pants may have fallen from mainstream popularity, but they have remained the dandy’s winter legwear of choice. They’re comfortable and casual yet somewhat smart, which puts them in a unique position whereby they can look equally at home with sneakers and a T-shirt or casual tailoring.

The degree of stretch provided by the cord fabric makes them more akin to sweatpants than jeans on the comfort spectrum, and the thickness of the wales (that’s the name for the raised fuzzy strips) does an excellent job of insulating against the cold.

We think they look great with an unstructured blazer in a complimentary colour, a pair of loafers and a classic wool overcoat.

Heavy Twill Chinos

Your average chinos simply aren’t going to cut it when the weather is at its coldest. Of course, that’s not to say you should stop wearing chinos entirely during the winter. After all, we’re talking about one of the most versatile and classic legwear options there is – it would be a shame to simply cast them aside for the entire season.

That’s why heavyweight twill chinos, with their thicker fabric, are our go-to smart-casual trousers during the colder portion of the year. Wear them with an Oxford shirt, knitted sweater, desert boots and a parka for a foolproof smart-casual winter look.

Heavyweight Sweatpants

For cosy days around the house, nothing does it like a proper pair of heavyweight sweatpants. These aren’t your average high-street joggers – they’re ones made from super warm fleece-backed jersey cotton that’s thick, soft and perfect for keeping warm.

We love these things because they’re surprisingly versatile if you’re bold enough to get a bit creative with your styling. Granted, you probably aren’t going to be wearing them to a black-tie dinner, but do they always have to be paired with a slouchy hoodie and a pair of sneakers? Absolutely not.

Try throwing on some knitwear, an overcoat and a pair of comfortable casual shoes like a pair of Clarks Wallabees to give these laid-back pants a completely different feel.

Cargos

Cargo pants are all over Instagram Explore feeds and TikTok For You pages at the moment, but you don’t have to be a Gen-Z fashion influencer to get involved. These practical pants aren’t specially designed for cold weather or anything like that, but the extra pockets are great for stuffing a hat or a pair of gloves into, and if you really do need some extra warmth, there are plenty of heavyweight twill and insulated options out there to be had.

Wear them with sporty or workwear-inspired pieces like hoodies, chore coats, boots and sneakers.

Tailored Wool Pants

Unfortunately, you can’t just scrape through the cold season in a pair of sweatpants or cargos, as much as you might like to. There will be those occasions here and there where a little more effort is required. Maybe you’re attending a winter wedding, or maybe you’re heading out somewhere fancy for a date. Either way, you’ll need some legwear that’s up to the task, and there’s no trousers better suited than a pair of classic tailored wool pants.

Wool pants are warm, smart and surprisingly versatile, plus there are lots of different styles and cuts to choose from. So even if you don’t ordinarily wear tailoring, you can probably find something that you like and that works on your body.

You could go slim, loose, high-waisted, pleated, even slightly flared if you’re a daring dresser – the list is endless.

Technical Hiking Pants

You don’t have to be an intrepid mountaineer or a hardened hillwalker to appreciate the cold-weather benefits a pair of techy hiking pants can bring to the table.

Not only are they supremely comfortable, they’re also durable and practical and some are even insulated with fleece-back softshell fabric or treated with a water-repellent coating, making them ideal for the cold weather.

Insulated Casual Pants

If you’re the type of person who feels the cold then regular old winter pants might not cut it. In that case, you should go for something more heavy-duty, perhaps with a bit of insulation to trap body heat and seal out the cold.

You probably think of insulated pants as the sort of things you would wear to go skiing, not on a regular everyday basis. But thankfully there are some stylish options out there that are right at home with your casual day-to-day clothes.

Uniqlo makes some fantastic options in this category, ranging from fleece-lined cargos to synthetically insulated technical pants, all of which are perfect for tackling the worst of the winter weather in style.

Raw Selvedge Jeans

There’s no better time than winter to invest in a pair of proper jeans. We’re talking thick Japanese or American raw denim that gives you an upper body workout to pull out of the closet. These types of jeans are ideal for the cold weather because of the denim’s thick, tight weave, which makes it great at blocking out wind and trapping warmth.

The best part is that jeans like these get better with age. The more you wear them, the more they’ll mould and conform to the shape of your body. And as the indigo dye rubs off in high wear areas it creates beautiful fades and a patina that is unique to you and your lifestyle.