The everlasting styles every man should be shod in come winter.
Men have been wearing boots for at least 3,000 years, so we’re going to hold our hands up here. What follows does not include calfskin ankle boots designed by Inca warriors or mankind’s original winter men’s boots, which were made by Inuit tribes and decorated with seal intestines. Sorry about that. What it does include, however, are classic 20th-century designs that do what the best boots for men have always done: they work.
Fashion rarely gets more functional than this. Whether you’re talking military stompers, steel-capped workers or rootin’-tootin’ cowboy boots, they’re all built for purpose. The fact that they look good is, in most cases, a happy coincidence.
These days, you might not work on the docks, and your feet probably only need protection from deceptively deep puddles. But if you want to look rugged and stylish at the same time, in footwear that will last longer than almost anything else in your wardrobe, these are the best pair of boots for men you should have on your feet.
1. Grenson Triple Welt Fred Boot
Having shod the feet of Allied troops in two world wars, traditional Northamptonshire shoemaker Grenson is more than qualified to offer the smart, functional footwear when you need to look suited and booted. The firm, founded in 1866, was among the first to adopt the famous Goodyear welting technique, but its triple welt boot proves that it’s still innovating more than 150 years later.
Launched in 2014, the triple welt gives the brand’s classic brogue boot an even chunkier sole, adding width and height to a design that was already hard-wearing and nigh-on watertight. Designed to last you winter after winter, the sole of these winter boots will wear as slowly as the dapper brogue details date.
How To Style Them
“Grenson provides practicality with its hiking-inspired eyelet lacing and sturdy Goodyear-welted soles, but also through offering a contemporary vibe with brogue detailing,” says Mr Porter shoes buyer David Morris.
For meetings in the city, the pebble-grain leather pairs expertly with flecked wool trousers, but don’t mistake them for a strict Monday-to-Friday option. “These boots will always give a rakish look when teamed with denim jeans,” says Morris.
2. Clarks Originals Desert Boot
A classic variation of polo-inspired chukka men’s boots, the key difference is the casual and exceedingly comfortable crepe sole. Nathan Clark, whose grandfather founded the eponymous shoe store in 1825, first noticed the style on the feet of British troops in Myanmar in World War II. He sent sketches back home, and the design has remained virtually unchanged since 1950.
“As [footwear] staples go, this is quite possibly one of the most important pairs you’ll own,” says Sarah Ann Murray, a stylist who has dressed the likes of Samuel L. Jackson and Kit Harrington. “What’s particularly relevant about them, given the ankle height, the weight of the boot and its fabric, is that they complement all heights and builds and pretty much all trouser styles, even suit trousers.”
How To Style Them
“Clarks offers a handsome colour palette with clean lines and unfussy finishings, though you can’t go wrong with chocolate brown if you can only pick one,” says Murray. “They’re perfect weekend attire, great paired with casual trousers or smarter jeans and offer a cool alternative to luxury sneakers.”
3. Dr. Martens 1460 Boot
A bona fide cultural icon, this is one of the best boots for men – famously worn by The Who’s Pete Townshend and a whole generation of skinheads – is about shit-kicking rebelliousness. It’s punk. It’s self-expression. It’s one of the ultimate best boots for men. So it’s funny that it was dreamt up by a German bloke with a dodgy foot. Dr. Klaus Maertens came up with the idea of an air-cushioned sole while recovering from a foot injury. At first, the innovation appealed mainly to elderly women and postmen, but then came the 1960s and 1970s, and with them, counterculture’s adoption of workwear styles, turning them into a stylish boot.
Today the 1460 boot (named after the date production began – 1 April 1960) is available in dozens of finishes, numerous collaborations, lightweight soles or – if you really want to rebel – vegan leather. “It’s one boot we all ought to own, never throw away and let that classic yellow stitching and cherry finish patina to perfection,” says Murray. “Dr. Martens bridge the gap between rebel style and hardcore functionality. But it’s their unconventionality that forms part of the appeal. Decades of nonconformists usurping the latest sneaker trend, or overpriced bourgeois luxury boots, has elevated DMs to an almost cult-like status.”
How To Style Them
“When you want to add just a nod of inner rebel and a confident edge to your ensemble, they’re perfect for rocking with an upscale workwear look, or tapered pleated trousers and a casual jacket,” says Murray about the chunky boot.
“Then for a full off-duty model look, of course, skinny jeans, a leather jacket, check flannel shirt, or any one of the above will complete the punk roots of this boot – but you don’t have to be Joey Ramone to wear them with panache.”
4. Timberland Original 6-Inch Boot
Nancy Sinatra presumably approves of Timberland’s iconic style because this boot was made for walking. Thick treads and a cushioned ankle make for a comfortable hike, while sealed seams keep the rain from leaking through that famous wheat-yellow nubuck. But, 40 years after they were first designed, the 6-Inch is, if anything, more comfortable on the tarmac than the open countryside, still making it one of the classic best boots for men.
“They are proof that function and fashion can, in fact, go hand in hand,” says celebrity stylist Alex Longmore. “They stood the test of time on the style front, are de rigueur in the wardrobes of seriously successful American rappers and are a favorite with the likes of David Beckham and his son Brooklyn.” As well as appealing across the generations, this boot also strolls between fashion tribes. Outside of hip-hop, you’ll also find them in workwear outfits, while the range of colors they’re now available in means they work with all kinds of tonal winter looks.
How To Style Them
“The reason they are so popular is they are masculine,” says Longmore. “These legends look best worn with casual clobber.” So put your pleated trousers away and make like Kanye in some relaxed-fit jeans with a simple T-shirt and bomber jacket.
5. R.M. Williams Chelsea Boot
Chelsea boots were first designed by Queen Victoria’s bootmaker J. Sparkes-Hall in 1851 as an alternative form of riding boot, with an elasticated ankle that made them easy to slip on and off. The high society connection survives to this day, but such an elegant boot is tougher than it looks.
“R.M. Williams’s Chelsea boot was built for durability and comfort to withstand the demands of the Australian outback,” says Morris. “The fact that these handcrafted boots are still worn and celebrated today highlights the level of expert craftsmanship,” Morris says. “Investing in a pair of these will guarantee you lasting style and substance.” Today the silhouette may be more synonymous with menswear bloggers than Mick Dundee, but its origins should be all the proof you need that the Goodyear-welted style is as resilient as it is dignified.
How To Style Them
Despite the Chelsea boot’s outback credentials, resist the urge to team them with a ripped shirt and cork hat. One of the few best men’s boots you can wear with a suit, the design is nevertheless more comfortable a couple of dress codes down. Ideal for getting your date-night outfit off on the right foot, wear them with slim-fit jeans or tailored trousers, some fine-gauge knitwear and either an overcoat or leather jacket, depending on the season.
6. Red Wing Classic Moc
These days you’ll more likely see Red Wings on the feet of creatives and baristas, but the brand’s moc toe design was first made for farmers and factory workers in the mid-20th century working in muddy conditions. It comprises reassuringly sturdy uppers on a lightweight crepe sole with minimal tread underfoot to reduce the mud that would cling to the boots at the end of the working day.
How To Style Them
What was originally made to wear with overalls today looks best with another workwear staple: denim. The round moc toe with contrasting white soles suits a look that mixes pinrolled indigo jeans, a flannel shirt, and a worker jacket altogether. If you have to clock on, you might as well look good.
7. Belstaff Storm Leather Boot
This British brand’s leather boots would become synonymous with motorcycle racing, flying, the world wars, and much more during its lengthy history. With ambassadors like David Beckham and Ewan McGregor, Belstaff went from strictly racing boots made to maintain a level of protection while racing (and providing comfort) to becoming a world-renown fashion brand, branching into leather jackets and other goods.
The Storm leather boot itself is a lightweight version of the famous Belstaff Trooper that takes cues from the military leather that would’ve been used for soldiers trekking in warmer climates. The lightweight EVA and rubber wedge sole provide great traction, offering foot protection in slippery conditions. Mixed with calf leather and Cordura nylon, these boots are sturdy, sleek, and perfect to wear in wet weather.
How To Style Them
Channel your inner biker with a crisp leather jacket, plain white t-shirt, and a pair of dark-washed jeans. Opt to wear either a straight leg or skinny fit so that you can tuck into the boots or roll up the hem to meet the top of the boot.
8. Church’s Suede Chukka Boot
Established in 1873 in Northampton, Church’s started as a small, family-owned factory and would go on to become a bold, innovative, and award-winning shoe brand that would adorn the feet of the British Monarchy, among others, while growing into an international phenomenon after joining the Prada group in 1999. If royalty can wear them, how can they not be the best boots for men?
Their suede chukka boot was originally created using crepe-soles and suede uppers to be used by soldiers during the campaigns in North Africa during WWII. Nowadays, these ankle-cut shoes are worn as a casual boot during the warmer months.
How To Style Them
This boot style should be reserved for casual, weekend outings. Pair them with chinos, a loose button-up or upgraded t-shirt, and a pair of brown sunglasses for a summer stroll in the city.
9. Tricker’s Stow Country Boot
The 100% born-and-bred Northampton shoe brand builds their boots to last — and their Stow Country boot is their most iconic design yet. Recognizable for their seven eyelet designs, these waterproof boots feature a leather lining and either a traditional leather sole or a Dainite sole for more practicality.
If you decide to invest in a pair of Tricker’s Stow Country boots, you can expect a boot that will last. Made from start to finish in their factory, each pair of boots takes about eight weeks and 260 processes to complete, with each material being able to be traced back to its source. Even his Royal Highness, The Prince of Wales, is an avid customer of the shoe brand.
How To Style Them
Even though it started off as a country boot, they are now worn everywhere. Pair them with a fun pair of long socks, indigo denim pants and a tweed blazer for a sophisticated, old-school look.
10. Carhartt Wedge Boot
Mostly used by men in construction and other hard-on-the-feet jobs, Carhartt boots can handle all terrains, providing protection and comfort to those who wear them. Depending on whether you’re using them as work boots, hiking boots, or just casual boots, the wedge boot (either steel toe, composite toe, or non-safety toe) is designed with oil-tanned leather and waterproof, breathable materials that keep feet dry and fresh.
How To Style Them
If you aren’t wearing these waterproof work boots on a worksite (and thus can avoid wearing mandatory work clothing), style these boots with ruggedness in mind. Think light-wash denim, thick flannel, and a comfy winter jacket for a cold-weather look that will have you ready for sloshing around in the snow, sleet, and mud.
11. Alden of New England Indy Boot
Founded in 1884 in Massachusetts by Charles H. Alden, this New England, family-owned shoe brand survived the Great Depression, WWII and more due to their high-quality dress shoes, as well as their venture into orthopaedic and medical footwear. Luckily, they also got into the boot game.
Their Indy boot is a classic – this authentic work boot has waxed leather uppers, a full-glove leather lining, steel shank, and oil-resistant outsoles. It also features moc-toe stitching and comes in a variety of colors.
How To Style Them
The Indy boot is versatile, you could either dress it up with nice pants, a jacket and a button-up, or you can dress it down with trousers and a comfy cardigan. You could even go rugged with denim and flannel. They tend to be a bit classier than other work boots, so when pairing them with an outfit, make sure they don’t outshine too much.
12. Crockett & Jones Coniston Derby Boot
Also founded in Northampton (this area really knows its boots!), Crockett & Jones have continuously made a name for themselves in the boot industry — especially with their Derby boots. A Derby boot is a fully lined, high leg, and more substantial boot with variations similar to a Derby shoe, and the Brecon version from Crockett & Jones takes all of that and more. With a Dainite rubber sole and from their lasting variations 341, this boot is both stylish and durable.
How To Style Them
Much like the desert and chukka boots, these ankle-cut derby shoes can be worn in a more casual setting. However, with the dark brown leather, you can potentially pair them with a more formal outfit, like a suit or blazer combo. As long as the colors mesh, then you will be golden.
13. Florsheim Plain Toe Gore Boot
Started in 1892 in Chicago, Florsheim has been at the forefront of trends since its inception, becoming some of the United States’ first squared-toe shoes as well as being a boot supplier during both world wars. Their retail stores also revolutionized the shoe industry by bringing shoes out of the back rooms and into stores for customers to see.
With prices that don’t break the bank, their boots are both stylish and affordable – especially their Plain Toe Gore Boot. The boot design combines modern materials with the comfort of a fully cushioned Ortholite footbed in a classic Chelsea boot design. You can choose between smooth leather or crazy horse-type leather upper, and it has a durable rubber sole to help you trek in style in any type of weather.
How To Style Them
These boots are great for when you need a hybrid dressy casual look. Style one of the best boots for men for a date night, class reunion, or casual work event, these boots paired with dark jeans or trousers (lean towards a skinny fit) and either a button-up, cardigan, leather jacket or denim jacket, will have you looking the part.
14. Season Three Ultralight Hiking Boot
Season Three is the brainchild of two MIT graduate students who decided to ditch software for physical products, putting their time and energy into creating the perfect all-weather boot in a sustainable manner. This led them to create the Ultralight Hiking Boot, their take on the popular European hiking boot. Minding their carbon footprint and keeping their manufacturing in Northern Italy, the Ultralight Hiking boot is one way to look good while trekking up a mountain or traversing the city.
The boot includes temperature-regulating wool to keep your feet warm in any and all situations and is made with 100% waterproof calfskin leather upper and Ortholite insoles for maximum comfort.
How To Style Them
If you’re hitting the trails, pair your boots with a warm sports jacket or flannel, sweatshirt and either joggers or light-wash denim. If you’re planning on wearing them in a less muddy scenario, pair them with some dark-wash denim and a leather jacket or sleek winter coat and sweater combo.
15. Nick’s Boots Urban Drifter Boot (Made to Order)
Nick’s Boots out of Spokane, Washington introduced their staple work boots back in 1964, solidifying their spot in the sustainable, durable, and American-made boot department — and their classic 6-inch work boot, the Urban Drifter, is a representation of that. Built from USA-sourced Horween leather (the legendary Horween Tannery in Chicago), the boot has leather insoles that mold to your feet and a Vibram lug rubber outsole.
How To Style Them
These boots are best for working or playing outside and should be avoided when you need a more formal or dressy shoe. Pair these work boots with jeans and a retro t-shirt for a laid-back, casual look.
Men’s boots FAQs:
Which is the best boot in the world?
It’s hard to pinpoint the perfect boots, but this list gets pretty close. From casual boots to hiking boots to rain boots, any of these pairs above would make a solid staple in your wardrobe.
What are the best hiking boots for men?
The Season 3 Ultralight Hiking Boot, the Belstaff Storm Leather Boot, and the Timberland 6-inch work boot are all great options when looking for a hiking boot.
How much is a good pair of boots?
Depending on the style and brand, a good pair of boots can range from $100 to several hundreds of dollars.
