It’s long been said that the arrival of fall marks the return of “real dressing.” That doesn’t mean dressing well comes easy in the colder months, though. The Highsnobiety Fall Fit Toolkit is here to help you through the transition to (literally) bigger and better clothing.

We subscribe to the ethos that pants are the true foundation of any good outfit. In fact, trousers are so powerful they have spawned subcultures, ignited outrage, and even triggered state sanctions.

Below, we’ve put together a primer on the most important pant shapes in modern menswear, from pocket-heavy cargo pants to the long-mistreated likes of the flare and boot cut.

Boot Cut

For more than a decade, the boot cut jean lived in the trash heap of mid-2000s history, buried in a pile of Von Dutch hats and Juicy Couture sweatpants. However, thanks to the post-ironic gusto of Martine Rose and Balenciaga, the silhouette has seen a welcomed comeback, riding the waves of Y2K nostalgia. Usually turned out in denim form, the boot cut has a straight-tailored upper, tapered at the knee but opening wider toward the ankle for that baggy finish.

Clement Rodeo Bootcut Denim Jeans

Clement Rodeo Bootcut Denim Jeans

$370

Acne Studios

Buy at Mr Porter
Trouser

Trouser

$200

Darryl Brown

Buy at Highsnobiety

Skinny

When Hedi Slimane debuted this season’s Cosmic Cruiser show, the world was shocked to see such trouser maximalism from a man credited with inventing the skinny jean in his collections for Dior Homme in the 2000s. Cigarette pants, skinny jeans, drainpipes — whatever you call them, you’ve likely got an opinion on this silhouette. Undoubtedly the world’s most divisive pant shape, the skinny trouser has been worn by The Beatles and banned in North Korea by Kim Jong-un. Even so, a new generation of artists who dip into punk and goth style, such as Playboi Carti and Lancey Foux, still defy supreme style leaders.

Plissé Skinny Trousers

Plissé Skinny Trousers

$315

Issey Miyake

Buy at Browns
Slim-Leg Leather Trousers

Slim-Leg Leather Trousers

$2690

Saint Laurent

Buy at Matchesfashion

Cargos

First seen on the legs of the British and US military way back in the 1930s and '40s, the cargo has ridden a pretty consistent wave of reappropriation since they were picked up by hip hop artists and rave-goers in the '90s. Modern menswear still can't put them down — and it's probably the fact they're so damn functional that's to blame. Good for carrying snacks and other vital essentials.

Pants

Pants

$500

Stone Island

Buy at Highsnobiety
Bauhaus Stretch-Cotton Cargo Trousers

Bauhaus Stretch-Cotton Cargo Trousers

$910

Rick Owens

Buy at Harvey Nichols

Capri

Is it a short? Is it a pant? That much is contested, but this silhouette has been making waves since designer Sonja de Lennart conceived the Capri back in the ’40s. The Capri is identified by its leg-hugging fit and three-quarter-length build. Yep, those things.

Knit Shorts

Knit Shorts

$495

NAMESAKE

Buy at H. Lorenzo
Pocket Short

Pocket Short

$1075

NICOMEDE

Buy at H. Lorenzo

Flare

Flares, in all their ultra-tight upper and super-wide ankle glory, were the go-to choice of 1970s trouser enthusiasts, but they are a silhouette woven into an astounding number of subcultures from the late ’60s and far into the ’80s. Disco heads, glam-rockers, and football hooligans have all favored the flare. Gucci’s Alessandro Michele still won’t let them go.

Velvet Trousers

Velvet Trousers

$1300

Gucci

Buy at ssense
Wool Insert Lounge Pants

Wool Insert Lounge Pants

$850

Raf Simons

Buy at ssense

Straight Leg

Born out of the 1800s Gold Rush, ​​the Levi’s 501 was designed to be a sturdy pair of pants to serve railroad workers and cowboys. Taking a straight-leg, regular-waist form, the 501 became the uniform for the everyday. And so it remains, its timeless shape having birthed countless other straight leg followers — the 1960s’ Dickies 874 Work Pant, for example — that get the job done without any fuss or flare.

501 Original Jeans

501 Original Jeans

$100

Levi's

Buy at ssense
Original 874 Work Pants

Original 874 Work Pants

$70

Dickies

Buy at HHV

Wide Leg

Dormant for quite some time in menswear, we can credit the return of the wide leg pant to two key phenomena. High fashion’s obsession with the ’70s and its wide-bottomed trousers — see Gucci and its muse Harry Styles — being one. The other is the major influence of Japan, via Yohji Yamamoto, Rei Kawakubo, Junya Watanabe, and younger labels like Goopi or London's JW Anderson and Studio Nicholson, which favor the pantaloon wide leg — wide kneed and cropped.

Cotton Twill Pants

Cotton Twill Pants

$339

Junya Watanabe

Buy at Luisaviaroma
Wide-Leg Twill Trousers

Wide-Leg Twill Trousers

$645

JW Anderson

Buy at Harvey Nichols

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