Best boots for men: from Chelsea to cowboy

Boot season is upon us and, in 2020, they're not just made for walking.

Around since the days of ancient Egyptians (a pair of boots was actually found in the tomb of ancient Egyptian chief Khnumhotep), though all types of men's boots were first engineered for a function, be that the military backstory of the desert boot or the stirrup-primed heels of the cowboy variety, today they provide ample opportunity to flex some style muscle. 

Whether that's in runway-ready takes by Giorgio Armani and Prada or fine-tuned incarnations of a classic by the likes of Grenson and Church's, here we bring you a lowdown of the boots deserving of a place in every man's footwear rotation this season, with GQ's picks of the best you can buy. Start walkin'…

Chelsea boots

No boot comes with the year-round appeal of a Chelsea boot. With origins in the Victorian era, it's since boasted discerning A-list adopters from The Rolling Stones to Kanye West.

Not surprising, given its cross-appeal between formal footwear (made from leather or suede) and ease of slipping on thanks to the loop-pull tag and lateral elasticated panels. Every man should own at least one pair.

Hiking boots

At the forefront of the outdoor function meets high-fashion trend, the humble hiking boot has undergone a serious makeover in recent years.

While this kind of footwear is done to best effect from brands that seamlessly blend performance elements into completely wearable shoes (see Camper and Red Wing, for instance), everyone from Prada to Valentino has now tried its hand at the hiker.

Given their durability and utilitarian appeal, it's an investment that'll stand the test of time (especially if you're predominantly treading pavement over mountain peaks).

Desert boots

No boot better treads the smart/casual divide than a desert boot. Popularised by Clarks in the late 1940s, they're inspired by a military-style boot introduced in the Second World War, made in Cairo's Khan el-Khalili bazaar.

They're unlined, ultra-durable and on the better value side of men's bootmaking just make sure you go over them with some Crep Protect before their first outing.

Cowboy boots

A winning combination of function, heritage and Wild Western romance made the cowboy boot the footwear of choice for a rebel generation.

Later, in the 1970s, Mick Jagger, Bruce Springsteen and Jimi Hendrix took the reins, followed more recently with some more than “all right, all right, all right” styling from Matthew McConaughey and modern style icons such as Orville Peck.

The rodeo resurgence dips in and out of fashion seasons and will forever inject some rock'n'roll flair into an outfit.

Bovver boots

The chuky bovver boot came into fashion in the late 1960s and, with its steel toe and sturdy design, soon earned itself a bad rap when it become associated with skinheads and hooligans.

Thankfully, punk rock made its stamp on the bovver boot and today this style is the perfect footwear to give a look some edge.

The most well-known boot of this style is without doubt the Dr Martens classic. 

Jodhpur boots

Similar in its silhouette to a Chelsea boot, Jodhpur boots have a decidedly more saddle-bound history, first designed in the 1920s as a riding boot for polo in the Indian city from which they get their name.

While some have the same elasticated panel as a Chelsea boot, they're more commonly fastened with a strap and buckle, making for particularly chic footwear worn with a pair of slim-fitting jeans.


For timeless elegance, always make Church's your first port of call on a boot hunt.

Its Bletsoe boot boasts a sophisticated shape, premium suede upper and a criss-cross strap complete with gold-tone buckle.

The slickness of them pairs perfectly with slim-fitting black jeans, while the rich brown hue of the suede is perfect for a country pub outing, meaning they're a boot that won't sit dormant in the box.


You might recognise this Grenson style from GQ's cover shoot with breakthrough British talent Michaela Coel last month.

The men's take is just as appealing a tall Derby boot with 14 eyelets. Don't be fooled by its bulk, it's incredibly lightweight and made from a waxy Black Chromexcel from Horween, a renowned Chicagoan tannery.

This is a boot for life, that'll just look better and better as the leather develops its own unique patina.

Clarks Originals

The Clarks desert boot is a classic that's been done in every incarnation imaginable. We're particularly buzzed for this beeswax leather take, though. True to the iconic style, the tactile upper sits atop a crepe sole in a rich brown, complete with those signature Clarks lace tags in the same materialisation. 


There's something very sci-fi about these Prada boots. A fashion house often described as ahead of its time, they look like they've been taken from the Prada flagship on the moon, 1,000 years from now.

Made from rubberised leather atop chunky rubber soles, wear them with an on-trend leather trench coat and you'll command any room (or, indeed, space station) you enter.

Common Projects

The clean Achilles white trainer of Common Projects is arguably the best iteration there is of this slick men's essential and its Chelsea boot closely follows.

First done in various shades of suede, these boots are typically minimalist and sophisticated, done in a luxurious full-grain leather and finished with one of the brand's signature gold serial numbers.

Brunello Cucinelli

A high-fashion take on the traditional hiking style, Brunello Cucinelli takes a classic silhouette and gives it some exceedingly luxurious appeal.

The headlines here are the deep polish of its dark-brown leather and the meticulous Italian craft, but take a look at the details and you'll really see what makes up this pair's worth, from the apron stitching to the rich brown suede heel tabs.

JW Anderson

If it's a fashion quirk you're after, look no further than JW Anderson.

The designer has perfected the art of a playful flourish that doesn't rely on gimmicks and these boots are a case in point.

An elegant ankle boot in smooth, black calf leather, the exaggerated stitch details to the front are just the ticket for a boot that becomes the star of any outfit.

Kingsman + George Cleverley

Buckle up, these boots mean business.

Part of the latest Kingsman collection, ahead of the next film in the franchise, our favourite movie/menswear crossover partnered with George Cleverley for these rather outstanding 1900s-style calf boots.

Made from smooth nubuck leather, five gold-tone buckles run up the side and it'd quite frankly be criminal to hide them underneath a trouser leg.


From its tannery on the Florentine outskirts, Guidi has been at the front of Italian leather craftsmanship since 1896 and it shows.

For leather as supple as that which has gone into these ankle boots, 124 years of expertise is exactly what it takes. We're particularly fond of the antiqued brass zip that runs down the middle.

Plus, to up the durability factor, optional rubber Vibram outsoles come in the box, but are best left to a cobbler to attach.

Giorgio Armani

Giorgio Armani has done a number on the classic, chunky military boot and the result is something that'll add edge to your outfits for many a boot season to come.

The ridged rubber sole amps up the bulk of these shoes to great effect, while the designer appeal comes care not just of a branded insole, but at the top of the multilayered sole unit too.

Red Wing

If you've ever been to Shoreditch, then you'll have seen plenty of these boots.

Red Wing have been adopted by men with perfect moustaches and lumberjack shirts over in the East London village and, to be honest, we can see why.

Robust, easy on the eye and long-lasting (Traction Tred outsoles and Goodyear welt make sure of that), the American beauties are worth investing in.


Crafted from a blend of cow and goat leather, these boots from All Saints have a minimalist design aesthetic and include a thick sole for some added height, should you want.


These black Grenson Brady Colorado boots hit the nail on the head of the hiking boot trend, which we reckon isn't going anywhere anytime soon.

With lace-up fastening and silver tone eyelets, these are a super chic take on a Runyon Canyon essential and we advise against getting these muddy.

RM Williams

Australian company RM Williams has been manufacturing shit-kicking boots designed for the hardcore terrain of the outback since 1932.

Now part-owned by Parisian luxury goods conglomerate LVMH, the brand has for SS20 teamed up with renowned industrial designer Marc Newson to create a line of more city-appropriate boots.

This quartz suede pair being an excellently spring-ready case in point.

DISCLAIMER: The Views, Comments, Opinions, Contributions and Statements made by Readers and Contributors on this platform do not necessarily represent the views or policy of Multimedia Group Limited.

DISCLAIMER: The Views, Comments, Opinions, Contributions and Statements made by Readers and Contributors on this platform do not necessarily represent the views or policy of Multimedia Group Limited.