Men have been wearing boots for at least 3,000 years, so we’ll put our hands up. What follows does not include Inca warriors’ calfskin ankle boots or mankind’s first winter men’s boots, which were fashioned by Inuit tribes and ornamented with seal intestines. I apologize for the inconvenience. It does, however, include classic 20th-century styles that do what the best men’s boots have always done: they work.

Fashion doesn’t get much more practical than this. Military stompers, steel-capped labourers, and rootin’-tootin’ cowboy boots are all made for a specific purpose. In most situations, the fact that they appear good is a lucky accident.

You might not work on the docks anymore, and your feet probably only need to be protected from deceptively deep puddles. However, if you want to look robust and stylish while wearing footwear that will last longer than virtually anything else in your wardrobe, these are the greatest boots for men to wear on their feet from fantastic, tried and true companies.

The 5 best boots for men

1. Grenson Triple welt Fred boot

Grenson, a traditional Northamptonshire shoemaker, is well-qualified to provide smart, useful footwear when you need to look suited and booted. The company, which was formed in 1866, was among the first to use the well-known Goodyear welting process, but their triple welt boot demonstrates that it is still pioneering more than 150 years later.

The triple welt, introduced in 2014, provides the brand’s traditional brogue boot an even chunkier sole, adding width and height to an already hard-wearing and watertight construction. The sole of these winter boots is designed to wear as slowly as the elegant brogue details date, so they will last you winter after winter.

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 says Mr Porter shoes buyer David 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.”

“Clarks offers a handsome color 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 that borders on a combat boot, but is ultimately its own type entirely.

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.”


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.

“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.


Regardless of the Chelsea boot’s outback credentials, avoid the impulse to pair it with a ripped shirt and cork hat. Despite being one of the few finest boots for men that may be worn with a suit, the style is more comfy a few dress codes down. Wear them with slim-fit jeans or tailored pants, fine-gauge knitwear, and either an overcoat or leather jacket, depending on the season, to start off your date-night wardrobe on the proper foot.