A fully-stocked shoe rack is just as important as a well-balanced wardrobe. Good footwear sets the tone for any outfit, and while the right pair of shoes will do the trick some of the time, certain occasions call for something a little more robust.
Boots make up a huge percentage of your potential footwear options. They’re comfortable, casual, provide protection from the elements and can completely change the direction of a look when put in place of their less lofty counterparts.
No footwear selection could possibly be considered complete without at least a few key boot styles, and these are the only ones you should be considering, from tough-as-nails workers to elegant Chelseas.
Ordinarily, hiking and luxury are considered mutually exclusive. After all, there’s nothing particularly luxurious about clambering up a muddy hillside in waterproof trousers with your lunch strapped to your back. However, in the context of footwear, the two worlds have collided and spawned some very wearable results.
Luxury hikers offer all the comfort and practicality of a traditional leather hiking boot, but in a package that wouldn’t look out of place with a smart-casual outfit, or even relaxed tailoring at a push. They’re sturdy and rugged, but also elegant and refined. A real paradox of a boot.
To style them, keep the rest of your outfit relatively low key. These boots are a little out of the ordinary and command attention, so don’t let anything else steal the limelight. Raw denim, neutral knitwear and a simple overshirt layered underneath a winter coat should do the trick.
Classic, wedge-soled, moc-toe work boots are as all-American as apple pie, Abe Lincoln’s beard and hot-dog eating contests. These workwear workhorses are built to take a punishing on a daily basis and, as a result, are some of the most durable boots money can buy.
Brands like Danner, Thorogood and Chippewa all produce fantastic US-made options, but the most popular label manufacturing this style is Red Wing. This historic company provided boots for soldiers in two World Wars and has established a name for itself as the best in the business.
A casual style through and through, it should be worn as such. We’d suggest teaming a pair with other workwear staples, such as a flannel shirt, chore jacket and worn-in denim.
Black Derby Boots
On the whole, boots tend to be less formal than shoes. But Derby boots are the exception. This is a style of boot that is sleek and sharp enough to be worn with tailoring, yet wouldn’t look out of place with a pair of jeans at the weekend.
A Derby boot in black leather is about as close to the perfect all-rounder as it’s possible to get. If you’re going to buy one pair of boots to see you through the winter months, make it these. They’ll keep the weather out, look the part with everything in your wardrobe and last for as long as you take care of them.
It’s difficult to think of a way in which these boots shouldn’t be styled, but they excel as part of a smart-casual or business-casual outfit. This considered, try wearing them with a roll neck knit, wool trousers and an unstructured blazer.
Nubuck Work Boots
Another style that started life on the forecourt and kicked its way into mainstream fashion, the quintessential nubuck work boot is Timberland’s classic 6-inch boot in yellow. In the 1990s and early 2000s, this style was as popular among rappers and scenesters as it was among workmen.
The ankle-high lace-up has a rounded toe, chunky sole, comfortable footbed and additional practical design points like a padded leather collar around the ankle and, of course, that waterproof nubuck. The yellow version is, depending on your viewpoint, either iconic or done to death, but you can get various shades of brown and black, and not just from Timberland but any number of brands that offer similar styles.
Assuming you don’t need the steel toecapped version, it’s a surprisingly versatile boot. Pair it with jeans or combat trousers for a traditional take on workwear or channel the hip-hop look with relaxed sweatpants.
Hard to find but worth a hunt, Oxford boots have become a little scarce as dress codes go ever more casual. They’re about as smart as boots get, often realised in polished leather with the same closed lacing system as Oxford shoes. This belies a somewhat hardier backstory as this style of boot was a practical stomper for Victorian gents and city dwellers in the first half of the 20th century. You’ll see a few style crop in the Peaky Blinders wardrobe department, for example.
Check out faultless versions from Northamptonshire shoe brands like Cheaney and Crockett & Jones. Their modern versions are best worn with sleek tailoring and eveningwear but they’d also finish off a date-night outfit composed of wool trousers, a sleek roll neck and a smart overcoat.
Brogue boots began life in the country but they’ve found a comfortable second home in the city. Around 2013, at the peak of the heritage menswear revival, major cities were overrun by men in brogue boots, herringbone overcoats, turned-up selvedge jeans and chunky knits. That particular combo might look a tad costume-y nowadays but the boots themselves are still well worth your attention.
Characterised by patterned, punctured holes in the leather (originally designed to let water out), they come in the classic spectrum of tan, brown, oxblood and black. For a modern take, find a pair with a chunky commando sole. These will match with more trouser styles than traditional leather-soled versions – try them with wide-legged chinos or cords, alongside tried-and-tested jeans and wool trousers.
Suede Desert Boots
If the term “smart-casual” were a boot, it would most likely be this one. The desert boot is nothing short of a menswear icon and has been for many decades. First created by Clarks, this boot has, as the slogan puts it, often been imitated, but never bettered – and we’d be inclined to agree.
The Clarks desert boot is a design classic that has strode across generations, remaining relevant and stopping off at every conceivable youth subculture along the way. There are leather versions out there but suede is the classic choice. Go for the Cola colourway if you’re worried about spilling wine on them, sand if you’re not.
Team with smart-casual hero pieces like a light-blue Oxford shirt, chinos and a light jacket for best results.
Leather Chelsea Boots
Slick, suave and eternally stylish, there’s an air of cool around the Chelsea boot that every man should experience. This low-profile boot is smart but not without a hint of rock ‘n’ roll attitude. It’s the sort of boot that you use to dress up on a first date or kick over amplifiers on-stage while shredding your guitar. And believe us when we say that there aren’t many boots like that.
With a mid top shape, elasticated side panels and laceless design, the Chelsea boot is just the right amount of stripped back. It’s not crying out for attention, but at the same time never fails to be noticed.
To stay true to that innate rebellious streak, set a black pair off with grey slim-fit jeans, a Breton top and a leather biker jacket. Or, for something a little smarter, go for a blazer, knitted polo and dress pants instead.
Motorcycle / Biker Boots
The majority of boots that men wear for fashion today began life as something more practical, designed for a specific purpose. Most of these styles switch codes quite easily, but motorcycle boots are A Look. A big one that can’t quite shake the smell of engine oil. So if you’re not a motorcyclist yourself, with a wardrobe full of Belstaff and Barbour International, you’re not going to get much wear from them.
That said, you can find motorcycle-inspired boots that are a little easier to integrate. Look for leather styles that don’t reach halfway up your calves like some authentic biker boots do, but around six inches, like a typical work boot. Statement buckles across the front or zippers up the sides are the details to keep an eye out for. Denim, twill and leather are the boots’ natural bedfellows but if that feels a bit like Terminator cosplay, swap the biker jacket for a big puffer or parka instead.
Combat / Tactical Boots
Many classic boot styles took inspiration from the military, but nobody on the front line today is wearing high and heavy leather boots. Instead, modern armed forces – like police and other first responders – wear hybrid models that combine lightweight comfort and toughness with canvas sections, Gore-Tex coatings and details reminiscent of modern hiking shoes or even sneakers.
Brands like Danner make specialised combat boots alongside their lifestyle ranges and, as menswear’s obsession with function continues, this style has made advances into the civilian wardrobe, too. Kanye’s a fan, for example, and Ryan Gosling’s character in Blade Runner 2049 also wore a pair.
Want to enlist? Look up specialist brands like Rothco, McRae and Altama (although you’ll also find styles from Nike, Under Armour and Salomon). They’ll have a single colour, usually black or tan, cushioned insoles and breathable panels. On civvy street, wear them with other macho, functional pieces like shearling coats, workwear and denim.
Functional winter gear doesn’t come much more pragmatic than snow boots. Akin to a pair of hiking boots with the thermostat turned up, snow boots have the same outdoorsy aesthetic that is easy to incorporate into a modern casual wardrobe and, if you’re fond of winter walks or ski holidays, they mean you don’t have to buy something separate.
Let’s talk practicalities. You’re looking for seal-seamed waterproof uppers made from nylon or something similar. A removable, washable inner boot is preferable, made from felt, borg or fleece for toastier tootsies than you ever thought possible. If you’re actually going to use them in the snow, some boots may come with optional galoshes made from silicone. Stick with brands that have genuine outdoor heritage like Sorel, Columbia, Arc’teryx or Moncler.
For off-piste styling, wear with jeans, technical trousers, twill or combats, and a mix of workwear and outdoor layers up top.
Stacked/Cuban Heel Boots
Men in heels: discuss. We’re very much in the you-do-you camp, but we’d throw in the caveat that if you’re looking for something practical and easy-wearing, then you may wish to look elsewhere. Men’s heeled boots have, however, never gone out of style for many in the rock ‘n’ roll fraternity. They’re flashy, practically seeping with Jagger-esque testosterone and, if you’re on the shorter side, they’ll add an inch or two to your height.
The style is essentially an ankle-high leather boot on a stacked or Cuban heel. They may have a zip-up opening on the side but you can also get Chelsea boots with the same leg-up at the heel. The toe is pointed rather than rounded, and that kind of peacocking also extends to the leather. As well as staple blacks and browns, you’ll find styles in a patent finish, red or white colouring or, if you want to go full Nicolas Cage, snakeskin.
The only way to style these is with bravura. Lean into the Hedi Slimane look with skinny jeans or flared trousers, patterned shirts, tailored blazers and leather jackets. It’s only rock ‘n’ roll but, yeah, we kind of like it.
Yes, wellies have gone fashion and if that surprises you, you haven’t been paying attention. Designers have, in recent years, ransacked every corner of practical workwear for inspiration. Now you can pay designer prices for statement rubber boots made by the likes of Bottega Veneta and Off-White.
You’ll find a few calf-high styles in the traditional shape of a Hunter or Barbour Wellington, but more common at the fashion end of things are shorter ‘puddle boots’ – chunkier in style and more workwear inspired. Bold colours are not uncommon for directional streetwear styling, but a more wearable look comes from Chelsea-style puddle boots in neutral greens, greys and blacks.
Cowboy / Western Boots
There are some states in America where the cowboy boot has been on-trend since the early 1800s. For the rest of us, it’s a truly wild (west) look that comes and goes with the tides of fashion and pop culture. Western wear has had a moment in recent years, however, yet another workwear subculture plundered by mainstream designers.
It is, of course, a big look for those of us who aren’t rodeo riders or high-plains drifters. You can get authentic cowboy boot designs with swirling embossed patterns, but assuming you don’t want to look like Hank Williams, opt for plainer styles in suede and waxed cowhide that are more akin to a rough-riding Chelsea boot.
Check out brands like Frye, Rhodes and Tecovas for something authentic and style them unpretentiously with jeans, tees and work shirts.
Those luxury hikers might look great out and about around the town, but when it comes to actually scaling mountains, there are far better tools for the job. Keeping fit is a big part of looking and feeling good and there are few better ways to stay in shape than by getting out for a hike. This is why a pair of proper, purpose-built hiking boots is a must for any self-respecting gent.
Take care to really look into the specs when shopping for any type of performance footwear and ask yourself how you’re going to be using it. Is it waterproof? Is it stiff? Flexible? What sort of insulation – if any – does it have? What are the soles made from?
Styling is less important when it comes to this type of boot unless you’re very keen to make leave a good impression on any sheep you happen to pass while out there on the trail. Just make sure they fit and wear them with other practical, performance garments.