A Guide To Autumn/Winter’s Key Trouser Fits

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Stylish men come in all shapes and sizes, which can make sourcing a pair of trews a pain in the, well, trousers. A new pair of strides can transform a man’s wardrobe, and provide the perfect opportunity to switch up your look for the new season – September is January when it comes to wardrobe remixes.

So whether your faded, ill-fitting old reliables have finally bitten the dust, or you’re just in the market for a bit of a style re-boot, here’s a handy cheat sheet to the fits worthy of your wardrobe this autumn/winter, and how to best put them to work.

Skinny Fit

Skinny jeans and trousers are no longer the sole preserve of pubescent black-clad My Chemical Romance fans (hat tip, Hedi Slimane). And with everyone and their literal dad (here’s looking at you, Beckham boys) continuing to slide their legs into skinny cuts, the leg-enveloped look shows no sign of faltering. So we thought it high time for a refresher on nailing the basics of the fit that is – although maybe not always at the fore of fashion – inarguably here to stay.

First off, don’t take things to the spray-on extreme as circulation-compromising trews will only emphasize a wiry frame (or cling unflatteringly to a meatier thigh). Knowing your size and not trying to cram into something smaller has never been more important than when it comes to slimmer styles. Muffin tops and camel toes aren’t just for girls, so look for a pair of chinos or trousers that hug your legs through both the thigh and lower leg but which doesn’t pinch.

Whether you’re styling yours up with a Chelsea boot for a Harry Styles-certified look or just keeping things casual with a pair of black Chuck Taylors, the skinny fit is one of the most wearable trouser trends of the season, and with high-end brands like Saint Laurent and Balmain staying loyal to the narrowest of cuts, it’s clear to see we’re not quite ready to bid sayonara to skinny just yet.

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Men's Skinny Cut Trousers and Chinos Outfit Inspiration Lookbook

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Key Styles

Men's Skinny Cut Trousers and Chinos

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Straight Leg

Tired of momentarily losing feeling in your legs? Or maybe you want to actually have children some day? Then swap groin-crunching skinny fits for a straight-leg style.

Smart enough to be worn with a shirt and blazer, but more casual than super-slim trews, you can’t go wrong with straight-cut trousers. If you’ve not picked up a pair before, the onset of autumn is the perfect time to explore the limitless versatility these basic britches will bring to your wardrobe.

Streetwear types have been repping the style hard the past few seasons – combining with hoodies, bombers and thigh-grazing tees – so you’ll be in good company as you get familiar with the skinny fit’s comfier cousin.

For a smarter look to meet stricter dress codes, take inspiration from the men of Savile Row. A pair of straight-cut tailored trousers will be a loyal companion for many years, whether they’re smartened up with a coordinating blazer and monk-strap, or kept casual with a Stan Smith sans sock – so while you’ll find plenty of decent options on the high street, don’t overlook the lasting value of a bespoke approach.

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Men's straight-Leg Trousers and Chinos Outfit Inspiration Lookbook

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Key Styles

Men's straight-Leg Trousers and Chinos

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Wide Leg

Where outsized proportions meet Scandi-inspired minimalism, you’ll find wide-leg trousers. The maverick on this list, the wide leg has been gaining traction over the past few seasons, as some of the biggest names in breakthrough menswear – from Astrid Andersen to Craig Green – have put the fit front and centre in their collections. So it stands to reason that the appetite for exploded styles is slowly trickling down to the high street, moving in on straight and slim leg’s turf.

Minimalists, particularly, will want to get better acquainted with this roomier fit. It’s a powerful style with a striking silhouette, so let your trousers do the talking by keeping the rest of your look low-key in a muted colour palette.

When it comes to choosing the right pair for your body shape, a flared pair will complement a taller and slimmer frame, whereas if your legs are on the stockier side, opt for a slightly tapered wide leg.

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Men's Wide-Leg Trousers and Chinos Outfit Inspiration Lookbook

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Key Styles

Men's Wide-Leg Trousers and Chinos

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Tapered Jogger / Cuffed Trouser

Something wonderful has happened this year: relaxed, athleisure-inspired loungewear has become as appropriate for the office as off-duty. Thanks to our cultural obsession with sportswear, flanked by designers like Cottweiler and Nasir Mazhar focusing heavily on sports-inspired fits, it’s no wonder the tapered jogger has taken centre stage this season.

What does that mean for your trouser rotation? Well, it no longer consists solely of denim, chinos and smart slacks – now, you can pull on a whole stadium’s worth of tracksuit-meets-tailored trousers.

When it comes to styling up a pair of tapered joggers, you can either rock them with a sneaker and oversized sweat for a look that’s clean, fresh and the outfit-equivalent of lying on a couch or change tack to something smarter by mixing with a button-down shirt and classic camel overcoat to dial up the sharpness on your say so. Job done.

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Men's Tapered Jogger / Cuffed Trouser Outfit Inspiration Lookbook

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Key Styles

Men's Tapered Joggers / Cuffed Trousers

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