Winter Pants: The Alternative Trousers To Try This Season

Trousers maketh man, a great man once told us. Or was it manners? Whichever it was, we’re sure he’d agree that a good pair of winter pants can be transformative.

Though often overlooked in favor of the latest must-cop shirt or have-to-have-it jacket, a pair of well-fitting trousers can leave you to look taller (cropped styles do this particularly well), slimmer (tapered legs were invented by wizards, we can only assume), and just a bit more put together. Not to mention also having the warmest pants and being the envy of cold legs everywhere.

This is just as true in winter as it is in the summer months, though the colder weather means it’s important to choose a pair that’ll keep you feeling warm and looking fire. Fortunately, we know of six warm pants styles that’ll do exactly that.

Corduroy Trousers

For the past few winters, we haven’t been able to move on the high street for cords – and for good reason. “Corduroy is a great choice of winter fabric due to its sturdiness and warmth,” explains Julian Lloyd Jones, founder of East London tailor Casual Fitters. No way these reliable and warmest pants on the market can steer you wrong.

Originally used for factory uniforms as a durable, cheaper alternative to wool, corduroy has been a winter mainstay since the ’70s, the era the ribbed fabric is most synonymous with. For maximum versatility, Lloyd Jones advises a pair with a 10-12 wale, meaning 10-12 ribs per inch of fabric.

Cords Warmest Pants
Warmest Pants Cords from Billionaire Boys Club
Incotex Warmest Pants Cords
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How To Wear Them

A pair of rugged cords are an easy substitute for denim. Stick to a regular or tapered fit, leaning into the fabric’s workwear origins by wearing them with a sweatshirt, a utilitarian jacket, and big black bovver boots. When it comes to color, brown is the classic, but navy and khaki are more modern and easier to wear.

Warmest Pants Corduroy Look
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Moleskin Chinos

Moleskin falls under the same umbrella as corduroy and is essentially the same fabric without the ribs, again giving you one of the warmest pant options on the market. “Like corduroy, moleskin is a hard-wearing cloth originally worn by laborers during the colder months,” says Lloyd Jones. “Historically It has also been used in military uniforms, which is why you often see it in khaki greens and browns.”

With a similar napped finish to suede, moleskin trousers are soft, comfortable, and a good winter alternative to chinos – in some cases, the cloth is so tightly woven that it’s effectively windproof. “When shopping, look for a slightly looser cut due to the rigidness of the fabric,” suggests Lloyd Jones.

Richard James Moleskin Warmest Pants
Warmest Pants Moleskin Chino
Incotex Warmest Pants Chino Moleskin
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How To Wear Them

Done wrong, moleskin has the potential to veer into Jeremy Clarkson territory. Fortunately, it’s very easy to get right. Keep things casual and contemporary by teaming khaki moleskins with a simple crew neck jumper, a denim jacket, and trainers. As with anything textured, keep the pattern to a minimum, with a plaid shirt about as far as you want to go.

How to wear the Warmest Pants, Moleskin Chinos
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Flannel Trousers

Long a business-casual staple, flannel – a soft, fuzzy type of wool – is also a growing favorite among creative types, who’ve found that they look just as good atop a pair of runners as they do with more formal get-up. You want versatility in your wardrobe that not only says stylish but ‘damn, those are the warmest pants’ for the coldest days.

“It is often made in a slightly looser weave than traditional wool twills to create a softer feel,” explains Lloyd Jones. “This looseness means that it is often not as hard-wearing as traditional twill weaves, meaning it should be bought in a heavier weight (9 or 10 oz) so that they last more than one season.”

Saks Fifth Avenue Warmest Pants
Thom Browne Designer Flannel Warmest Pants
Hugo Boss Flannel Warmest Pants
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How To Wear Them

To achieve the off-duty architect look, choose a pair of cropped and pleated flannel trousers in classic grey melange as your starting point. Wear with a white Oxford shirt layered underneath a crew neck jumper, with either white tennis shoes or a pair of leather Derbies, depending on the occasion.

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Cargo Trousers

Like the Backstreet Boys and every other ’90s boyband, cargo trousers are back, alright. The 21st-century take features neater, more regimented pockets, and is more in line with the cargo trousers’ battle dress origins than it is with Top of the Pops. Cargo trousers, if worn right, can take you from work to play and from summer to the depths of winter where you’ll be eagerly reaching for a pair of those warmest pants.

“This time, cargo trousers are being worn in a slimmer fit,” says Sarah Gilfillan, a men’s stylist and personal shopper at Sartoria Lab. For winter, look for pairs in heavyweight cotton ripstop (an authentic military fabric) or smart wool, with Gilfillan recommending “a pair in a neutral color like black, olive or navy as a good base for weekend wear.”

L.L. Bean Classic Cargo Warmest Pants
Nike Cargo Warmest Pants
66 North Cargo Hiking Warmest Pants
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How To Wear Them

Play up the military associations by teaming your cargo trousers with a simple bomber jacket. “Just avoid having an overload of pockets on the jacket as well as the trousers,” Gilfillan advises. “And if you choose a pair with elasticated hems ensure you have the right boots or trainers to wear them with [i.e. ankle height and not too bulky].”

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Drawstring Trousers

There was a time when a pair of stretchy trousers was a sign of defeat for a man, an admission that he was past his prime. But fortunately, the dawn of athleisure-inspired streetwear has convinced us that the opposite is in fact true: that drawstring trousers are stylish, youthful, and not to mention, can be insanely comfortable and another set of the warmest pants in your wardrobe. The more relaxed styles on offer are ostensibly tracksuit bottoms in high-end fabrications, though smarter options have a more tailored fit with details such as pintucked pleats. “In either case, ensure that they fit well on your bum, and are not too baggy on the leg,” says Gilfillan.

Wax London Warmest Pants
Streetwear Designer Warmest Pants
A Days March Warmest Pants
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How To Wear Them

Drawstring trousers are practically the definition of smart-casual wear, so long as they’re cut from a smart wool or cotton blend. “I particularly like them with a fitted, fine-gauge sweater and smart leather trainers,” says Gilfillan. “If you’d like to smarten them up a bit more wear with a button-down shirt, fine knit cardigan, soft-soled brogues, and an unstructured blazer.”

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Check Trousers

Like pinstripes, checks are one of those classic menswear motifs that never really seem to go away. There are countless variations – houndstooth, windowpane, gingham – but the most versatile of all is a Prince of Wales check. “Originally known as a Glen Plaid check, the Duke of Windsor brought it into fashion in the early 20th century,” explains Lloyd Jones.

A crossing pattern of irregular checks, it’s most commonly seen in grey with hints of brown, green and/or red. Great for either casual or formal wear, these pants can take you inside and out and you can bet it will be one of your warmest pants. Lloyd Jones recommends that you seek out pairs where the check is woven into the fabric, rather than printed, as some cheaper styles are.

Warmest Pants in Wool Blend Green Check
Saks Fifth Avenue Warmest Pants in Plaid
Comme Des Garcons Warmest Pants in Check
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How To Wear Them

Pattern-clashing might be all the rage in Pitti, but for most men it’s best to just keep things simple. If you’re after a smart look, mix a pair of your new warmest pants (in a slim-fitting checked trouser) with a plain navy jacket, a roll neck, and a pair of black leather brogues. To dress down, swap the blazer for a field jacket and the brogues for high-top Converse.

Warmest Pants Check Trousers
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