Men and boots go together like two peas in a pod. Predominantly worn in the colder months to keep feet dry and warm… and cemented to the ground, preventing falls on slippery surfaces, they’re a must-have item 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., and can be a perfect travel partner. As with any other footwear, boots come in various styles, materials (i.e. leather or suede) 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?
Boot Materials
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.
Know Your Boot Styles
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
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
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.
Hiking Boots
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.
RELATED: Best Hiking Clothing Brands To Buy Right Now
Brogue Boots
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
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
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. 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. 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.Why are Chelsea boots so popular?
How do you wear boots with jeans?
What is the best way to stretch boots?
Some other helpful DMARGE stories about footwear:
Oliver Cabell
1/26Price: From $313
Sizes: 7-14
Material: Water resistant full-grain leather
Customer Reviews: “Love Oliver Cabell! These boots rock! I can wear them open and untied, Sox or no Sox. Took me no time at all to break in. Best birthday present ever! Thank you.”
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.
Allbirds
2/26Price: From $145
Sizes: 8-14
Material: ZQ Merino wool
Customer Reviews: “These shoes are just about perfect for California winter. They’re warm, sturdy, and offer both support and the comfort that I’ve come to associate with the Allbirds line.”
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.
Amberjack
3/26Price: From $195
Sizes: 7-13
Material: Full grain leather
Customer Reviews: “These Chelsea boots are phenomenal! Super comfortable fit. Great look. Classy , still casual but dressy. I love these boots.”
For some truly comfortable boots, you need to be checking out Amberjack. The American shoemaker has all of its footwear handmade in Portugal using the finest, sustainably-sourced leather. The company’s boot selection isn’t that expansive right now, comprising of only Chelsea boot styles, but they are available in a range of colours and made from both genuine leather and Italian suede.
What we particularly love about Amberjack boots is their price, falling perfectly into the affordable category. If you’re looking for some of the best and most comfortable boots for men, look no further.
Clarks
4/26Price: From $100
Sizes: 7-13
Material: Leather
Customer Reviews: “The thick crepe sole is bouncy and supremely comfy. The leather uppers start soft and get softer.”
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.
Cole Haan
5/26Price: From $180
Sizes: 7-16
Material: Leather
Customer Reviews: “Super comfortable after one day of wear. Narrow fit so I purchased the wide and they’re perfect. Light, comfortable, and great looking. I love them!”
American shoe and bootmaker Cole Haan produces footwear that is instantly recognisable, usually by way of interesting-looking outsoles. They serve a purpose, however, offering up cushioning, comfort and traction, with some unique style thrown in for good measure.
Take a look at these 4.Zerøgrand Hiker boots for example, serving up a completely weatherproof boot design that leaves your feet warm and dry, with a triple-density foam being integrated into the sole to assist with those extra long hikes.
Koio
6/26Price: From $395
Sizes: 7-13
Material: Italian suede
Customer Reviews: “Super comfortable with little to no break in. I gets the compliments!!!”
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.
Wolverine
7/26Price: From $170
Sizes: 7-14
Material: Premium waterproof full-grain leather
Customer Reviews: “Husband absolutely loves the boots. He says they fit perfectly, they gave grip on the bottom for if the ground is wet/snowy, loves the color and the support. Great work boots, wears them everyday!”
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.
Red Wing Shoes
8/26Price: From $515
Sizes: 7.5-14
Material: 100% Calf leather
Customer Reviews: “Built to last ⋅ Very competitive price ⋅ Goodyear welt seems fairly infallible”
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
9/26Price: From $292
Sizes: 5-12
Material: Leather
Customer Reviews: “Soles are extremely durable ⋅ Reasonably priced boots.”
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.
Church's
10/26Price: From $1,290
Sizes: 5-13
Material: Calf suede
Customer Reviews: “The shoes may be good quality but for the price.”
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.
Common Projects
11/26Price: From $70
Sizes: 39-47
Material: Calfskin
Customer Reviews: “They are more for casual wear, but they are super comfortable and great for most terrains.”
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.
Rhodes
12/26Price: From $250
Sizes: 8-13
Material: Full-grain leather
Customer Reviews: “These boots are very stiff upon opening & am slowly breaking them in 😅. They appear very well made & durable. I tend to be rough on my boots & these looks rugged for the long haul.”
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.
Moncler
13/26Price: From $755
Sizes: 39-46
Material: Leather
Customer Reviews: “Though these chunky leather hikers are more on the utilitarian end, they are still finished to a very high standard.”
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.
Grenson
14/26Price: From $409
Sizes: 6-12
Material: Leather
Customer Reviews: “Their shoes are comfortable, the leather is good quality, they’re generous with the sizes especially if you’re wide footed.”
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.
Paul Smith
15/26Price: From $595
Sizes: 6-12
Material: Leather
Customer Reviews: “These boots are gorgeous. Understated and sleek.”
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.
Danner
16/26Price: From $440
Sizes: 5-14
Material: Full-grain leather
Customer Reviews: “The shoes fit like a glove and are VERY comfortable even on day one. I suspect it will take several months to fully break them in and then they will be even more comfortable and stylish given normal wear and tear. I am so glad that Danner still makes a boot like this!”
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
17/26Price: From $539
Sizes: 7-13
Material: Leather
Customer Reviews: “excellent quality and very comfortable.”
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
18/26Price: From $160
Sizes: 6-15
Material: Better leather
Customer Reviews: “These boots are perfect for the cold winter. They are warm and fuzzy, so comfortable and true to size.”
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.
John Lobb
19/26Price: From $2,207
Sizes: 2-17
Material: Leather
Customer Reviews: “Impressively solid sole-work, though very clearly at odds with the fiddle-backed and sculpted soles aesthetic on modern shoes..”
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.
TAFT
20/26Price: From $295
Sizes: 6-15
Material: Jacquard Weave, Leather
Customer Reviews: “Stylish, well designed and comfortable.”
Founded in 2014, TAFT is a men’s footwear brand specialising in unique, bold shoe designs. TAFT shoes are produced in Spain and Portugal with premium textiles ranging from suiting wool, to woven upholstery fabric, to Charles F. Stead leather. Meticulous in their work, intentional in their designs, and obsessive over what makes the cut, TAFT has become well-known for their extremely well-made unique men’s shoes.
TAFT has a huge range of extremely well crafted boots, all made with premium leather, in a variety of unique styles that’ll make you stand out in a crowd.
Beckett Simonon
21/26Price: From $400
Sizes: 7-13
Material: Water-repellent suede
Customer Reviews: “I wore these boots out for the first time last night and they looked and felt great, as expected.”
Beckett Simonon, founded in 2011, believes in the power of well-made products which make you look and feel your best; products you can wear year after year, and repair rather than replace. Which is why they produce stylish high quality shoes, available for unrivaled prices and made with responsible manufacturing processes.
They have a HUGE collection of handsome, well-constructed boots all made with premium materials, and available in multiple styles and colours.
Jack Erwin
22/26Price: From $248
Sizes: 7-14
Material: Suede
Customer Reviews: “These boots are super smart looking, they definitely go just fine with a suit — unusual for Goodyear welted shoes.”
Founded in 2013, Jack Erwin was launched with one sole purpose: to create truly timeless men’s shoes. Partnering with the finest factories and artisans in the world, creating custom styles, and eliminating costly markups and middlemen that drive up the costs of other quality dress shoes, Jack Erwin produces some of the best men’s footwear available that’s surprisingly affordable.
Jack Erwin’s fantastic boots range features clean lines and luxe, all-season materials, making Jack Erwin’s boots perfect for the city, no matter the weather.
Ace Marks
23/26Price: From $350
Sizes: 5-15
Material: 100% Full-grain calf skin leather
Customer Reviews: “Fantastic shoes! Really comfortable, absolutely beautiful leather. Definitely the best pair of dress boots I’ve owned.”
Founded in 2012, Ace Marks believes that men shouldn’t have to spend obscene amounts for a handcrafted world-class shoe. Using modern technology, to cut out middlemen and their markups, Ace Marks can directly deliver cleverly contemporary, utterly luxurious, and comfortable shoes (which rival those of the top luxury brands) all at an attainable price.
With a huge range of men’s boots, available in multiple style and colour options, you’re sure to not only feel comfortable but also make a lavish powerful statement when rocking a pair of Ace Marks boots.
Kodiak
24/26Price: From $165
Sizes: 7-13
Material: Full-grain waterproof leather
Customer Reviews: “On my third pair of Thane boots, and they are everything I look for in a pair. Look great (in my opinion) last years, element resistant, and incredibly comfortable.”
Canadian brand Kodiak has been producing high-quality boots since 1910. Renowned for using only the finest fabrics & materials and their impeccable craftsmanship, Kodiak is one of the best boot brands on the market.
Kodiak has a huge range of men’s boots, although they are all on the rugged, outdoorsy side of the boot world. Perfect for hiking, bonfire get-togethers, or just if you want a super masculine look.
The Original Muck Boot Company
25/26Price: From $170
Sizes: 7-13
Material: 100% Genuine farmwork leather
Customer Reviews: “Great product as always from Muck. Comfortable and solid durability. Can wear as casual around town as well.”
The Original Muck Boot Company was founded to build the most protective, most comfortable, most reliable boots on the planet; no matter what the conditions. Today, the brand has been providing 100% waterproof boots that withstand the muckiest situations in every season for over two decades.
The Original Muck Boot Company has a huge range of men’s boots that includes steel capped boots, gum boots, ankle boots, tall boots, and leather boots, all of which are completely waterproof and will keep your feet dry!
Veldskoen
26/26Price: From $180
Sizes: 4-15
Material: Full-grain leather
Customer Reviews: “Very comfortable, high quality materials.”
All of Veldskoen’s shoes are handcrafted in South Africa with locally sourced, premium materials. The brand is committed to crafting shoes that are not only ethically and responsibly made but, feel crazy comfy and provide effortless daily style.
Veldskoen has a small but mighty range of men’s boots that are extremely stylish and well-made.
