How To Wear Wide-Leg Pants And Look Good Doing It

Men's Fashion

It’s not hard to remember a time when wide-leg trousers were considered one of those beyond-the-pale pieces that fashion designers periodically tried to foist on sceptical menfolk, perhaps out of boredom, or “for banter”.

Sure, wide-leg trousers made an impact on the runway. Okay, so they created a striking silhouette. And yes, they had swagger. But off the runway? They were an unacceptable breach of breeches conduct. Sheer pantaloon-acy, to be given an equally wide berth.

But as you perform your umpteenth series of pulse squats to squeeze into your skinny-fit jeans, or dislocate your ankle to get your foot through that drainpipe leg opening, do you ever stop to think that there might be another way? That it might be time to broaden your horizons?

Menswear’s brains trust certainly thinks there’s room for a roomier trouser style. Many of today’s biggest trends prefer a wider leg: street-friendly skatewear, pleated mid-century styles and voluminous tailoring are all generous and flattering below the belt.

The Rise Of Wide-Leg Trousers

Revolutionary though they may seem, wide-leg trousers are not exactly a novel concept. ‘Oxford bags’ as they became known date back to the 1920s, when stunting undergrads at the eponymous university wore trousers with hems of up to 40 inches in circumference – and looked like dons. Frank Sinatra did wide-leg trousers his way in the 1950s, as did Marlon Brando. And David Bowie did frankly whatever the hell he wanted in the 1970s – which included wide-leg trousers.

“Yes, but Bowie was a sartorial extraterrestrial,” you cry. True, but even for us style earthlings, wide-leg trousers are more wearable than you probably imagine. They are undoubtedly a statement – but that means you don’t really need to try that hard.

Thankfully, fashion is cyclical, and wide-leg trousers are getting another long-overdue play. After years of spray-on oppression, high-end fashion houses and streetwear labels alike are freeing men from their stonewash straightjacket. And crucially, dissenting designers challenging the constricting doctrine are practising what they preach by wearing them, proving that they look unusually good in real life too.

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4 Ways To Wear Wide-Leg Trousers

None of this is to say that to be fashion-forward, you need to run a belt through two tents. Yes, the runway end of the trouser fit spectrum has lurched dramatically flappier. But that means that, for those who’ve spent the last decade peeling their trousers off every evening, it’s time to inch up into something roomier. Here are four ways to pump up the volume.


For those new to the relaxed-leg fit, casual looks are the easiest way to experiment. “Start off with a classic colour or fabric, such as navy or black in cotton or a wool-blend,” says Mr Porter style director Olie Arnold. “Denim is also an easy way into the trend.”

To balance out all that extra down below, think simple. “Wear with a well-fitting crew-neck T-shirt or Henley. Many wider trousers have traditional front pleats and a higher waist; tuck the top in to highlight this feature.” It’s a move approved by Jude Law, back in his Dickie Greenleaf days.

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It’s not just the cut of clothes that has been gradually relaxing over the last few years. Dress codes have also loosened up, making relaxed-leg trousers an excellent way to nail everyday smart-casual.

The trick here is to keep everything else simple so that the trousers are the only wild card in the deck. Think tonal shirts, roll necks and muted bombers. Not only will you feel confident enough to wear them that way, but you’ll also be doing ‘a thing’ without really doing all that much.

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All that extra material necessitates a nipped-in waist, whether in the form of a cropped jacket or a tailored one, to prevent you ballooning. Luckily, looser-fitting trousers can work in business-casual offices, provided you make up for the more relaxed fit by dialling up the styling. “A well-cut pair of pleated trousers can bring a rakish touch to a formal look by pairing with a deconstructed blazer, a crisp shirt and some polished Derby shoes,” says Arnold.

When wearing a blazer with relaxed-fit trousers, you can also alleviate the impact by rolling the hems, so the trousers swing, rather than puddle. “A slightly shorter pair of wide-leg trousers in black can be ideal for the office when worn with a tucked in slim shirt, to balance the voluminous shape.”

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Could you imagine suddenly being able to move around with ease. Put things in your pocket. Sit down without a cheese-cutter bisecting your crotch. Sounds truly liberating, right? It is. And it’s a feeling some have known for decades.

Whether it’s the streetwear crowd or the skate lot that regularly riff on workwear, wider legs have long been the go-to. Not that you need to resemble a Slim-Fast ‘after’ photo to get the look. Simply prioritise trousers cut from thick cotton twills and denim rather than anything that belongs on Savile Row, and pair these with relaxed (but not baggy) logo sweatshirts, hoodies and chore jackets.

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6 Tips For Wearing Wide-Leg Trousers

Create Contrast

Unlike skinny jeans, which can make it seem as if your torso is teetering on a pair of cricket stumps, relaxed-fit trousers add some heft to the lower part of the body. Just don’t make the mistake of echoing that up top.

“The main mistake people make with wide-leg trousers, is going wide everywhere else,” says Giles Farnham, head of the River Island Style Studio. “If wearing relaxed trousers, everything else should be fitted, otherwise you look like you’re wearing a big brother’s hand-me-downs. Wide trousers worn with a fitted shirt looks considered. Wide trousers and a baggy shirt just looks scruffy.”

Pleats Are Your Friend

Once reserved for men who had more hair coming out of their ears than the top of their head, pleated trousers have recently been rescued from the bingo hall by designers. This subtle crease down the front of the trouser leg is a godsend to men who are no strangers to the squat rack, as it adds extra fabric around the thigh and seat. Which also means you can breathe easy when the mercury starts rising.

“With a slightly roomier cut, pleated trousers are perfect for relaxed, summer dressing,” says Arnold. “Make sure the trousers have a slightly cropped profile, which will ensure they feel current and on trend. Keep the rest of the look simple with a crisp shirt, T-shirt or piece of knitwear, so those well-executed pleats remain the focus.”

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Nail The Fit

The graph of fit against physique follows a bell curve. To pull off spray-on-skinny or David Bowie loose requires a body that would work on a runway. But move to the middle with relaxed and straight cuts and things get more forgiving.

However wide you go, getting the fit right is key. With that much extra material already on show, the world doesn’t need to see your underwear as well. Make sure the trousers or jeans hit near your waist, not hips, or you’ll look like a kid who got dressed out of dad’s wardrobe (and not in the good way).

Pick Your Shoes Wisely

As is the case with most looks, the right shoe can make or break this trend. The original baggy boys were students at Oxford in the 1920s, who wore extreme wide-leg trousers over their knickerbockers, which the university had outlawed. While we’d avoid using yours to smuggle contraband underwear, it is worth stealing one move from the OGs; a pair of shoes that don’t get drowned out.

“The wider silhouette in the leg is complemented by a wider, round toe like you get on a pair of sneakers,” says Farnham. “Avoid slightly pointier, narrow shoes such as loafers as they will jar with the loose fabric and end up looking like you’ve been taking style tips from Chabuddy G from BBC Three’s People Just Do Nothing.”

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Consider Fabrics

There’s a fine line between Marlon Brando and Margery from Bradford (no offence, Margery). When it comes to straight rather than tapered-leg trousers in particular, staying on the right side of history comes down to the fabric.

To avoid the mum abroad look, think heavier materials to keep everything from billowing in every gust of wind. “In winter, try a richer wool fabric like flannel and in summer a thicker linen,” says Farnham. “Thicker materials also gather well on the shoe.”

Stick To Neutrals

Wide-leg trousers are a statement in their own right, so steer well clear of loud colours or printed styles and opt for an understated neutral design instead. Black, grey or navy versions are a great place to start as they will slot effortlessly into your wardrobe and combine well with everything you already own.

Alternatively, if you want something decidedly more casual, try a pair of relaxed-cut chinos in stone or khaki. They will look superb teamed with a white Oxford button-down, linen shirt or plain tee.

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