Guys and boots go together like two peas in a pod. Predominantly worn in the colder months to keep feet warm and cemented to the ground, preventing falls on slippery surfaces, they’re a must-have item of footwear that all men should have in their wardrobe.
Naturally, they can be worn in warmer months too, with Chelsea boots, in particular, proving to be one such pair that have year-round versatility. As with any other footwear, boots come in various styles and colours, and some pairs are made for more specific purposes other than just making you look good as you stroll down the street.
So what should you be looking out for next time you’re out boot shopping?
The majority of boots – or at least, the ones you’re going to want – will have a leather upper. Being made from genuine leather means the upper of the boot will naturally form to the shape of your foot over time, making them so comfortable you’ll never want to take them off. Leather is also a great material for protection against rain and snow, as it has water-repellent properties. Of course, the more you spend, the better quality leather you’ll get in return.
You can also find boots made from other materials such as suede, which are geared more to being worn in warmer months as there is less chance of them being blasted with rain, potentially causing damage.
As for the sole, well, if you’re going to be wearing your boots in winter you’re going to want a material that will provide Formula 1 car levels of grip. If that’s the case, avoid leather – you’ll be slipping and sliding all over the place. Instead, look out for rubber soles. In case you’re conjuring up images of huge, chunky soles, fret not, for some bootmakers integrate a slim rubber layer on the bottom of their boots to keep them look smart.
The world of men’s boots is rife with various style, each with its own history and purpose. That also means some work better with certain looks better than others.
Chelsea boots are instantly recognisable, owing to their elasticated side panels. The design was first conceived by J. Sparks-Hall, Queen Victoria’s personal shoemaker, and became popular among horse riders, as well as being regularly used for just walking in, with the elasticated panels making them easy to slide on and off (helped by a small tab on rear). They weren’t originally called Chelsea boots in the early days, but their popularity with residents of the upmarket London borough, and famous faces such as The Rolling Stones, is believed to have led to their now-famous nomenclature.
Work boots were, as their name suggests, worn by workers to protect their feet from all manner of debris and weather types. No longer as they confined to the building site though, as pairs from brands such as Timberland have gained cult status. Work boots tend to have the chunky rubber soles we mentioned earlier, so are more than ideal for wearing on cold, wet and snowy days as they’ll make sure you’re well-planted to the ground and keep your feet well-protected.
When we say hiking boots, we don’t mean boots used for actual hiking up mountains with a full set of camping gear strapped to your back. Instead, we’re talking about the much more fashionable hiking boot. Similar to work boots in that they’re designed to offer optimum protection, they can also be used to complement rugged, outdoorsy outfits. Moncler is a particular champion in this arena, but other luxury brands have their own noteworthy interpretations.
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Brogue boots are an extension of the Brogue shoe, exemplified by their use of perforations for detailing. Brogue boots can be found in a range of colours, and depending on which colour you go for will determine the sort of outfit they can be paired with. If you really want to prove to everyone you mean serious boot business, invest in a pair with a Goodyear welt. This is a strip of leather or rubber that runs around the entire outside of the boot, connecting the upper and the sole. It gets its name from inventor, Charles Goodyear Jr.
Chukka boots are another style with a deep history, dating back to World War II, where they were worn by British soldiers serving in India. Traditionally made from suede (referred to as Desert boots), they can also be made from leather and feature either rubber or leather soles. The name chukka is said to come from the game of polo, describing a period of play. Chukka boots are ankle-high, open-laced, unlined and feature just two or three pairs of eyelet holes.
Men’s Boots FAQ
Why are Chelsea boots so popular?
Chelsea boots are known for their versatility. They look good paired with skinny jeans or a tailored suit. Their timeless shape and design make them a must-have for men of all ages and styles.
How do you wear boots with jeans?
The fit of your jeans must complement the style of your boots. A pair of slim leg pants is always a safe choice, but for chunkier boot styles, you may opt for a straight or relaxed fit. Your jeans must fit comfortably over the top of your boots.
What is the best way to stretch boots?
You may use a hairdryer to help expand your boots. Just wear a pair of thick socks and blow dry over the tight spots. Freezing also helps. You can stretch your boots half a size to a full size.
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Oliver Cabell, like Common Projects, is famed for its minimalist sneakers that will improve your style game tenfold. But being a footwear company, it should come as no surprise to know it also has a solid range of boots, to boot. The main balk of its collection comprises service boots, with designs inspired by the military. Materials include leather sourced from Spain, and rubber for the soles sourced from England. The soles are attached to the leather uppers via a Blake stitch, which sees the outsole stitched directly to the insole, allowing them to be lighter than those that use the Goodyear welt.
American-New Zealand footwear brand Allbirds puts a prominent focus on sustainability and ethical processes in the production of all their shoes and boots. Design-wise the company's boots rock clean, minimalist silhouettes with virtually no branding in sight. Instead, you can choose from a variety of colours and either wool or eucalyptus tree fibres being used for the main material. They may not be the hardwearing, Goodyear-welt sporting boots like some others on this list, but with waterproof qualities and flexibility to conform to your feet, they'll remain comfortable all day long.
Clarks is a British-based shoe manufacturer founded in 1825 that has since amassed a strong global presence. Not just the supplier of shoes for school children, Clarks is home to a vast range of classic shoe and boot styles, all of which are made to a high-quality yet don't charge extortionate fees. It's more famous and recognisable shoe is without doubt the Desert boot, a style which the company is credited as inventing, but a style based on the boots worn by British officers during WWII. Clarks' Desert boot can be had in both leather and suede, with the latter perhaps being the more popular version. It can be had in a range of colours, so you could effectively have multiple pairs for multiple uses: dark brown or black for date night, and tan or light blue for daytime walking. Clarks also makes some seriously capable hiking boots, as well as Chelsea and brogue styles.
Yep, American sportswear giant Nike makes the list of best boots for men, contrary to what you might have thought. The 'Just Do It' advocate isn't just in the sneaker game, as it has a varied range of boots all ready to tackle the great outdoors. Features across the range include water-resistance, rugged materials incredible traction. The perfect blend of style and substance.
British shoemaker Grenson is known globally for its high-quality and well-designed boot styles. The company is so committed to boots, that it covers off virtually all the main styles: Chelsea, hiking, chukka and brogue. Not only does Grenson use fine-grain leather and suede materials, but it has also made the switch to vegan-friendly materials that maintain it's dedication to providing the last word in quality. Prices for Grenson boots start at $360 and can reach into the $600 bracket, but for your investment, you'll be rewarded with a pair of boots that will last you for years.
American-Italian footwear brand Common Projects doesn't solely make must-have white sneakers. The brand actually has a varied range of footwear, which includes a number of boot styles. The relatively young company (it's just 16 years old) certainly knows how to put together a decent pair though, using high-quality leather for both its leather and suede models. In true Common Projects style, the style, size and colour are displayed by way of numbers along the heel, and as with its minimal sneakers, Common Projects boots serve a suitably stylish upgrade to any outfit.
American footwear brand Koio was conceived to bring together a European flair for design with the American 'can-do' attitude. Koio is predominantly a sneaker brand, ticking off both high and low-top styles, but they have recently expanded into boots too. Designed to tackle the great outdoors, Koio's boots have incredibly thick soles that offer exceptional shock absorption and grip, while also being lightweight so you don't feel like you're dragging a couple of weights around.
Red Wing Shoes
Red Wing Shoes hails from Red Wing, Minnesota and gained instant popularity after it became the main boot manufacturer for American soldiers during WWI and WWII. Its boots are primarily associated with heavy work and as such, produces a dedicated range of workwear with extra toe protection.
You're more likely to invest in the Heritage collection, with the Classic Moc proving to be its most popular style. Its chunky sole not only provides optimum traction, but a Goodyear welt also gives ample protection from wet weather. A range of colours married with its iconic yellow/orange laces only add to the style credentials.
Dr. Martens, or "Docs" or "DMs", are unmistakable in their look. Even if you've never owned a pair, you will instantly recognise the British brand (founded by Klaus Märtens) for its yellow stitching, chunky soles (which are air cushioned) and associated with British punk and goth culture. Those who wear them swear by their exceptional comfort, with the leather upper moulding to the wearers' feet. The 1460 is the most popular style, but the company has diversified into other styles, such as the Chelsea and has also made the switch to using vegan leather for some models.
Another British brand, this time, Church's. Founded in 1873, Church's was actively involved in the general development of the footwear industry, which it did so in between the two World Wars. It has since been taken over by Prada, which should give you an idea as to how high-end of a brand it is – its brogues were used to dress Pierce Brosnan's James Bond.
The company has a varied range of boot styles, encapsulating Chelsea, hiking, desert and brogue. Materials vary too, not only are you treated to leather and suede, but you can even find pairs made from canvas. Prices can edge close to $1,000, but for the very finest materials and expert craftsmanship, they're worth every cent.
Wolverine is an American footwear company founded in 1883, with full production starting in 1903. Not only does it have its own eponymous label of footwear, but it also produces other well-known brands including Hush Puppies, Merrell and tradesman-favourite, Caterpillar. Wolverine boots are unmistakably pitched in the work boot category, being offered in tough-as-nails designs with thick rubber soles. The company integrates its own technologies to ensure its boots remain comfortable for hours on end and to be highly durable against all types of weather, as well as whatever a working site can throw at them.
Rhodes is a brand stocked exclusively by outdoor gear specialists Huckberry. Rhodes itself claims its product aren't going to compete with any expensive dressy pairs you may own, but rather it claims its boots are ones you can rely on to withstand daily wear and tear. Rhodes boots are made at family-run factories in either Portugal or Italy, and made from calf leather and suede. They're all re-soleable too, so will happily adorn your feet for years on end. The Rhodes range includes chukka boots, Chelsea boots and everyday work boots, all of which won't break the bank.
When we said fashionable hiking boots at the beginning of this piece, the first brand that has to come to mind is Moncler. The French luxury goods brand has always been associated with alpine pursuits and cold weather, and as a result, produces a range of boots to help you tackle whatever dire conditions may come your way. Hiking boots with gunmetal-tone lace hoops are the main draw to Moncler's boot collections, but you'll also find desert boot styles and Chelsea boots too.
Paul Smith is a British brand that really knows how to dress a gent well. Started by Sir Paul Smith in 1970, the brand has seen existential growth in the decades since. While the brand may be iconic for its multi-coloured stripe design, that hallmark doesn't actually make it into the boots it produces.
Instead, you're treated to a number of classic silhouettes, including Chelsea, hiking, chukka and dress boots. We'd argue Paul Smith is a brand best associated with the Chelsea boot style for its upmarket connotations, and Smith's pairs are made from high-quality smooth leather and can easily be paired up or down with dress pants or jeans.
Also high up on the list of famous hiking boot manufacturers is Danner. The Oregon-based company has been making boots for close to a century and has always remained committed to delivering pairs that last a lifetime, are comfortable for long periods and allow you to get out and exploring the great outdoors.
The Mountain Light Boot, for example, was first launched in 1979 and has remained in the company's repertoire ever since. The latest iteration receives a Gore-Tex treatment to provide a waterproof liner, while speed hook laces make sure you get a truly snug fit. They're capable on the mountains and handsome enough to wear as a daily pair.
R.M. Williams are the boot of Australia. Heavily associated with the Outback, the company originally started out producing leather goods for the horse riding industry. Since its founding in 1932, R.M. Williams has gone on to become a global luxury retailer – and is now owned by the LVMH Group. R.M. boots are still made by hand today at the workshop in Adelaide and are noted for the fact they're made out of a single piece of leather. With the association with Outback culture still remaining true, R.Ms will be able to withstand whatever you can throw at them.
Timberland, along with brands such as Dr. Martens, have generated itself a cult following, "hey, should I wear my Timberlands today?". The American company targets its product catalogue at those who love to live life in the great outdoors, and as such, its boots are made to withstand numerous weather conditions. Timberland boots are instantly recognisable by their logo on the heel and the colour we think all guys should go for is undoubtedly wheat nubuck.
The colour has been imitated by countless other brands, both budget and high-end, and for good reason: it works seamlessly with virtually all pant styles, especially denim. Add in total waterproofness, "anti-fatigue" technology to keep them remaining comfortable all day long and a rubber sole that will keep you glued to terra firma and you have yourself the perfect outdoor boot.
Saint Laurent is one of the largest and most well-known fashion houses on the planet, thanks in no small part to the fact it was the first couture fashion house to offer the general public a luxurious ready-to-wear collection. To this day, the brand continues to push boundaries, while still offering all the modern 'essentials' a guy could need. The Saint Laurent boot collection has something for everyone too (so long as you like Chelsea boots), whether it be a pair finished in classic black leather or a more daring pair finished in snakeskin. And considering the brand's reputation, they're priced incredibly competitively.
Continuing the theme of luxury British bootmakers, John Lobb has been producing high-quality leather boots for men since 1849. A separate John Lobb workshop that works independently from the London shop can be found in Paris, and this is owned by the Hermès Group, but both offer a bespoke, made-to-measure service.
They may be higher priced than some other brands on this list, but each pair is handmade, going through hundreds of steps before making their way onto your feet. The company's boots feature the Goodyear welt for the ultimate in weather-sealed design and, depending on the model you go for, will be made from fine-grain leather or suede.
Amiri was only founded in 2013 but has quickly earned itself a global reputation that exudes luxury. Creative director Mike Amiri has gone down a more expressive path in the design of his boots, opting for extra details such as a taller heel or using chains and other patterns to give the boots some character. It's with this in mind that they're perhaps not going to be to everyone's taste (and not everyone will be able to pull them off) but for those who like to rock the laidback L.A. look with an injection of indie rock (we're looking at you, skinny jean wearer), they could be your best accessory.
If only the finest quality leather is something you crave, Berluti is the brand for you. The French label is a master when it comes to using leather as a material, using not only conventional calfskin, but branching out to using kangaroo leather and alligator skin too. Its products have attracted famous faces including Robert De Niro, Timothée Chalamet and Andy Warhol. The majority of Berluti's product range can be recognised by its patinated leather, which is carried over to its range of boots too. That range includes Chelsea boots, Desert boots and hiking boots.