The Right Way To Wear Wide-Leg Trousers

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The Right Way To Wear Wide-Leg Trousers

Words by Ashley Ogawa Clarke

8 September 2025

01. Balance out your proportions

Wider pants often look best when their proportion is balanced out with a smaller item on top. Known as the “big pants, little shirt” look, it has become a go-to for trend-conscious guys over the last couple of years. It can be achieved by either downsizing to a fitted tank top or T-shirt if you’re cool with showing your body off. Or, for something on the safer side, a slightly cropped shirt, sweater or jacket.

For the latter, you’ll want to seek out brands whose silhouettes are boxy rather than long and drapey: CELINE HOMME’s knitted pullovers hit just above the waist, as do the sweaters by Story mfg. and the jackets by KAPITAL. Overall, this will help to create a silhouette that elongates the legs, looks intentional and avoid you getting swamped by excess fabric.

02. Choose the right footwear

“To counteract the roominess of a pair of wide-leg trousers, you need a slender shoe, like a penny loafer or a Gat sneaker,” Browne says. “Dressing well is all about playing with proportions – and throwing in a big, chunky shoe [with wide-leg trousers] doesn’t do that.”

If you want to get controversial and are prepared to defend your honour, hop on board with the biggest footwear trend of the summer: flip-flops. If anybody says anything, just show them Auralee’s spring/summer runway from this year, where the models wore flip-flops with wide-legged soft tailoring and looked excellent. Nobody argues with Auralee. As long as your tootsies are in good enough condition that they won’t elicit screams from the public, that is.

03. Get into painter pants

Painter pants, also known as carpenter pants, are durable trousers usually made from a thick cotton canvas in neutral shades like beige or cream that have a roomy, straight-leg fit. True to their name, they were originally designed for DIY-minded men who did lots of painting, chiselling and building with their strong, callused hands. (We used to be a proper country!) Nowadays painter pants are enjoying a renaissance among those of us whose hands are more used to carrying matcha lattes than mitre saws – but hey, they look great.

Search “canvas trousers” and delight in the bounty of pairs with double-knee detailing that you’ll find from workwear-minded brands such as Carhartt WIP, Cherry Los Angeles and Remi Relief.

04. Say “yes please” to pleats

For a more formal, dressy way to do wide legs, seek out pleated styles with a slight rise on the waist. “Pleated trousers require more thoughtful design, craft and material than non-pleated pants and are more expensive for a brand to make,” Browne says.

The drape on a pair of pleated pants also evokes a bygone time when guys really knew how to dress themselves. Have a gander at old pictures of Clark Gable and the Duke of Windsor for high-waisted wide-leg inspiration, as well as proof of the look’s timelessness.

For a great drape that also looks cosy, Browne recommends soft flannel fabrics made from wool or a cashmere blend. “For that, look no further than Loro Piana and The Row,” he says. When paired with an Oxford cloth button-up shirt or, when the weather gets cooler, an unstructured blazer or chore jacket, they will look effortless in the best way.

The people featured in this story are not associated with and do not endorse MR PORTER or the products shown