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Mens Cowboy Boots Square Toe

Types Of Boot All Men Should Own

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 ones you need in order to have all bases covered. From tough-as-nails workers to elegant Chelseas, here are the styles of boot no man should be without.

Luxury Hikers

Fracap M127 Roccia Sole Scarponcino Boot >
Grenson Brady Brushed-Suede Boots >
Diemme Roccia Vet Boot >


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.blob:

Moc-Toe Boots

Red Wing 875 Heritage Work 6″ Moc Toe Boot >
Oliver Sweeney Canhas Moc Toe Boot >
Grenson Rocco Pebble-Grain Leather Boots >


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

Church’s Wootton Calf Leather Lace-Up Boot Black >
Dr. Martens 1460 8-Eye Smooth Leather Boot >
Tricker’s Anniversary Edition Cruiser Tramping Leather 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.blob:

Performance Hikers

Sorel Atlis Axe Boot >
Le Chameau LCX Low Boot >
Scarpa Khumbu GTX Boots >


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.

Suede Desert Boots

Clarks Originals Desert Boot >
Oliver Sweeney Tavernelle Suede Desert Boot >
Tod’s 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 shirtchinos and a light jacket for best results.blob:

Leather Chelsea Boots

Saint Laurent Wyatt Leather Chelsea Boots >
Reiss Tenor Leather Chelsea Boots >
Church’s Prenton Chelsea Boot >


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.

World’s Greatest Bootmakers

Best Boot Brands for Men

“You get what you pay for” is a pretty good mantra to live by – especially where your wardrobe is concerned. Take boots, for example. If you’re tight with your money, you’ll be met with cheap leather (or worse, synthetic), flimsy soles and low-standard construction. Ultimately, that equates to footwear which won’t stand a chance against the harsh winter elements, will fall apart in a short space of time, and need to be replaced at further expense.

Alternatively, you could invest more and come away with something robust, handmade and built to last. It may be a bigger hit to your bank balance in the short term, but in the long run, you’ll get more for your money.

With that in mind, these are the bootmakers worth knowing and what they specialise in.


Best For: Quality British Boots With Character

Grenson Hadley Boot
Grenson Fred Commando Sole Brogue Boot Joseph Cap-Toe Burnished-Leather Boots
Grenson Fred Commando Sole Brogue Boot


They say practise makes perfect and Northamptonshire heritage footwear brand Grenson has certainly had its fair share. Founded by William Green in 1866, it was the first bootmaker to use the Goodyear-welt process (a layer of leather stitched to the bottom of the upper and then bonded to the sole) – a construction technique it still uses to this day and is now widely viewed as a hallmark of quality.

Signature styles include Derby and Chelsea boots, as well as some of the best brogues around.



Best For: Australia’s Finest Chelsea Boots

R.M.Williams Comfort Craftsman Suede Chelsea Boots Black
R.M.Williams Comfort Craftsman Suede Chelsea Boots Brown
R.M.Williams Gardener Whole-Cut Leather Chelsea Boots


Named after its founder, a travelling labourer and bushman who became a millionaire thanks to his leatherwork, Australia’s R.M.Williams is known the world over for producing some of the finest boots money can buy. One-piece leather riding boots are the brand’s most popular design and were revolutionary in terms of their construction when they first launched in the 1930s. Today, you can still find them alongside lace-ups and other classic silhouettes, all of which boast the brand’s characteristic rugged build quality and sleek good looks.

Buy now at FarFetch


Best For: Italian Craftsmanship

Velasca Pacciasass Suede Boots
Velasca Magut Brown Leather Chelsea Boots
Velasca Resegott Hiking Boots


Hailing from the small Italian city of Montegranaro, Velasca has quickly gone from a small artisanal shoemaking operation to a worldwide footwear brand without sacrificing any of the quality. Using the finest Italian materials and handmade techniques, the brand’s boot collection combines style with quality and durability in every piece. Highlights include the Giasee country boot and the classic Tirape lace-up.

Buy now at Velasca


Best For: Military-Spec Footwear

Danner Bull Run Boot
Danner Mountain Light Boot
Danner Light Boot


Hailing from Portland, Oregon, Danner is an American heritage manufacturer known for producing some of the toughest boots around. And that’s not just talk – the brand’s build quality and ruggedness has earned it a contract with the U.S. Department of Defense, making boots for the Marine Corps. And if they’re good enough for those guys, they’re good enough for us.

Buy now at Huckberry


Best For: Traditional Hikers

Fracap M120 Ripple Sole Scarponcino Boot
Fracap M120 Natural Vibram Sole Scarponcino Boot
Fracap M127 Cut Vibram Sole Scarponcino Boot


It’s been over a century since Tuscan craftsman Antonio Cappello made his first pair of hiking boots. It was a move that laid the foundations for a long-running family business that’s still going strong today. The brand is known for its boots’ traditional styling and use of fine Italian leather. And, in a move that has brought it bang up to date for modern times, shoppers can now completely customise their boots on the firm’s website and have them handmade to order.

Buy now at Threadblob:


Best For: Fashion Meets Functionality

Timberland Premium 6″ Boot In Yellow
Timberland Heritage 6″ Premium Boot
Timberland 6″ Premium Boot Black


Timberland’s signature six-inch yellow boot is nothing short of a footwear icon. In the time since it first hit shelves in 1973 everyone from weather-beaten workers to rap royalty has fallen in love with its robust build and rugged good looks. The yellow boot was originally designed to stand up to the cold, snowbound winters of New Hampshire – and it did just that, quickly becoming the basis for the entire Timberland brand and one of the most recognisable boots there is.

Buy now at FarFetch

Clarks Originals

Best For: Laid-Back Looks And Versatility

Clarks Originals Desert Boot
Clarks Originals Wallabee Boot
Clarks Originals Wallabee Boot Gore-Tex


It’s impossible to think of casual boots and not think of Clark’s. The brand is a British institution and its iconic desert boot is a timeless classic, unparalleled in terms of versatility and styling. It’s far from Clark’s only boot though. Other signature styles include the Wallabee and the Desert Trek, both of which feature its trademark crepe sole and minimal design ethos.

Buy now at SSENSEblob:


Best For: Countryside Pedigree

Tricker’s Stow Brogue Derby Boot
Tricker’s Burford Leather Boots
Tricker’s Henry Brogue Chelsea Boot


Another Historic British shoemaker flying the flag for Northamptonshire, Tricker’s has been on every self-respecting footwear connoisseur’s map since 1829, when the brand was the maker of choice for heavy-duty country boots and shoes for England’s estate owners and landed gentry. Today it’s still very much doing its thing, and thanks to some modern tweaks and the odd collaboration here and there, it’s one of the coolest bootmakers there is.

Buy now at MR PORTER

Red Wing

Best For: Classic American Work Boots

Red Wing 875 Moc Leather Boots
Red Wing Shoes 8085 Iron Ranger Burnished-Leather Boots
Red Wing 8859 Heritage Work 6″ Moc Toe Boot


If there’s one piece of footwear that perfectly encapsulates the vintage Americana workwear aesthetic it has to be a Red Wing boot. That combination of rich tan leather and white wedge sole is instantly recognisable and indicative of quality to those who know. Countless brands have attempted to better the Red Wing design and so far none have succeeded. If you’re after a pair of American work boots, why not skip the rest and go directly to the best?

Buy now at MR PORTER

Dr. Martens

Best For: Rock And Roll Attitude

Dr. Martens 1460 Smooth Boots
Dr. Martens Pascal Boot – Made in England
Dr. Martens Black ‘Made In England’ 2976 Chelsea Boots


Another Northamptonshire brand can only mean one thing: more quality boots. Dr. Martens is relatively young when compared to other shoemakers from the county, but what it lacks in heritage it compensates for in attitude. Although its boots were originally designed as workwear for gardening, Dr. Martens were soon adopted by various youth subcultures, earning them an “alternative” image which still holds true to this day.

Buy now at SSENSE


Best For: Comfort And Durability

Blundstone Dark Olive 1615
Blundstone Steel Grey 1910
Blundstone Walnut Brown 550


Hailing from Tasmania, Blundstone describes its boots as “the most durable, most comfortable ever made”. It’s quite a statement, but one that its products easily backs up. Plus, despite being one of the world’s most recognisable boot brands, Blundstone remains Tasmanian through and through, carrying out all of its design and production on home turf.

Buy now at Amazon

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