6 Alternative Winter Trouser Styles And How To Wear Them

Men's Fashion

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 slacks can be transformative. Though often overlooked in favour of the latest must-cop shirt or have-to-have-it jacket, a pair of well-fitting trousers can leave you 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. This is just as true in winter as it is in 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 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, trouser aficionado and founder of east London tailor, Casual Fitters. 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.


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 gilet and big black bovver boots. When it comes to colour brown is the classic, but navy and khaki are more modern, and easier to wear.

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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. “This time, cargo trousers are being worn in a slimmer fit,” says Sarah Gilfillan, 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 colour like black, olive or navy as a good base for weekend wear.”

Rag & BoneRag & Bone

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 [ie ankle height and not too bulky].”

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Moleskin Chinos

Moleskin falls under the same umbrella as corduroy, and is essentially the same fabric without the ribs. “Like corduroy, moleskin is a hard-wearing cloth originally worn by labourers 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.


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 pattern to a minimum, with a plaid shirt about as far as you want to go.

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Flannel Trousers

Long a business-casual staple, flannel – a soft, fuzzy type of wool – is also a growing favourite 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. “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.”

Mango ManMango Man

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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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, insanely comfortable. The more relaxed styles on offer are ostensibly tracksuit bottoms in high-end fabrications, though smarter options with 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.


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 [the Queen’s uber-stylish uncle] 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, Lloyd Jones recommends that you seek out pairs where the check is woven into the fabric, rather than printed, as some cheaper styles are.


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 slim-fitting checked trousers 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.

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