8 best men’s leather boots, from Chelsea to high-top styles

Give winter the boot with our tried and tested selection of the best suede and leather stompers

Paddy Maddison
Wednesday 23 December 2020 17:01
<p>With their sturdy soles, high-top design and durable uppers, these ankle-grazing wonders are perfect for tackling the cold weather in style</p>

With their sturdy soles, high-top design and durable uppers, these ankle-grazing wonders are perfect for tackling the cold weather in style

There comes a time every year when trainers and casual shoes struggle to perform. Rain water seeps through mesh uppers, gale-force winds batter exposed ankles and flat soles slip and skid over icy or wet terrain.

But what's the solution? Start wearing wellies for the commute? Strap a pair of crampons on to get to the pub?

Thankfully, there's a much more stylish alternative in the form of a classic leather or suede boot.

With their sturdy soles, high-top design and durable uppers, these ankle-grazing wonders are perfect for tackling the cold weather in style. That's why we thought now would be a good time to bring you a rundown of some of the finest options out there.

We searched high and low for the best of the best and put them through their paces to see how they stack up. We walked, we hiked, we strolled and we stepped, all while keeping an eye out for comfort, durability and style.

You can trust our independent reviews. We may earn commission from some of the retailers, but we never allow this to influence selections, which are formed from real-world testing and expert advice. This revenue helps to fund journalism across The Independent.

G.H. Bass camp moc ranger

Maine-based moc-toe footwear specialist G.H. Bass is best known for its weejuns penny loafers. They're great, but it's a crying shame the brand's boots don't get more attention if you ask us.

The ranger is the label's classic moc-toe boot and its good looks are matched only by its versatility. This boot wouldn't look at all out of place worn with soft tailoring and smart-casual outfits, yet it's still relaxed enough to slum it with jeans and a T-shirt at the weekend.

Comfort-wise it's a winner and we experienced only a minor breaking-in period when compared to most other leather boots of the same ilk. The uppers are soft, supple and smack of quality and the square leather laces bolster the boot's traditional New England looks.

Overall, a great-looking, comfortable boot from a brand with some serious shoemaking clout. After testing, we're confident in saying that the G.H. Bass ranger runs true to size. Go for your normal shoe size for a great fit.

Danner mountain light

These retro hiking boots from heritage American bookmaker Danner aren’t the cheapest of the bunch. But there's a very good reason for that: they're built to last and that's clear from the moment you take them out of the box.

Fully winterproof, the mountain lights come with a super-grippy, Vibram commando sole and a waterproof, Gore-Tex membrane to keep your feet warm and dry. They require a fair bit of breaking in – these are serious boots, remember – but it's a drop in the ocean when you offset it against how long they're likely to last you (we'd wager decades).

Plus, they look great. Like, really great. In fact, they're actually the same boots Daniel Craig wore for the alpine scenes in Spectre. Hey, if they're good enough for 007 in the Austrian Alps, then they're good enough for us tramping around rain-soaked streets here in the UK.

These fit true to size, but there is no removable insole, so if you want to add your own for comfort then we'd advise buying a half size up.

Clarks wallabee boot

What can we say about the Clarks wallabee that hasn't already been said? It's an icon; a true design classic; a suede-covered slice of footwear history. If you don't already own at least one pair, you should. And after testing out the boot version for a number of weeks, we'd say it's a great place to start your collection.

After the striking looks (we tested a rather spicy brick-red/orange option) the first thing that you'll notice about these boots is how comfortable they are. The wallabee is famous for its trainer-like feel under foot thanks to the soft, suede upper and crepe sole. And it's no lie. Most boots you can't wait to take off at the end of the day, but the wallabees you'll want to keep wearing.

Just make sure to give them a generous dose of suede protector before you go venturing outside. We'd say the wallabee boot fits true to size, so take your normal size for a perfect fit.

Kickers kick hi classic

Hey, the nineties called. They want their boots back. Yeah? Well tell them to do one because we're keeping them.

You might recognise Kickers’ kick hi from back when Ant and Dec were floppy haired teenagers as opposed to national treasures. But unlike many articles of dress from that particular era, this playful boot has stood the test of time, retaining a strong cult following over the years. It’s even managed to gain some streetwear clout thanks to much-hyped collaboration with high fashion’s favourite skate label, Palace, a few years back.

But that’s all by the by. The main things you need to worry about are comfort and looks. And it’s a big thumbs up from us on both counts. This is a cool, quirky alternative to more straight-laced, traditional boot styles, making it great for anyone seeking something a little offbeat.

It’s also a pleasure to wear. The unusual tread pattern combined with the upwards curve of the sole at the heel and toe make for a very comfortable walking experience. And of all the boots here, let’s just say these are the ones we’d want to be wearing if we had to sprint for the bus.

These boots run true to size. If you’re in between sizes, go up rather than down.

Red Wing moc toe boot

Whether you’re in a car mechanic’s garage in Detroit or a hipster coffee joint in Peckham, chances are a pair of Red Wing’s classic moc toe boots are only spitting distance away. Why the surprising crossover appeal? Well, they’re highly practical, durable and functional, of course, but they don’t half look cool too.

If we had to summarise this boot in one word, it would be “rugged”. These things are built to take a beating and the oil-tanned leather somehow winds up looking better with every wear. If you’re searching for an everyday boot that you can keep reaching for year after year, you’ll struggle to find better.

Like most proper boots, the Red Wings take a bit of breaking in. However, once you’re over that hurdle you’ll be left with a seriously comfortable pair of boots that’ll be with you for many years to come. These are pretty roomy in our opinion. We’d advise ordering a half size down for the best fit.

Ariat wexford waterproof boot

These classic Chelsea boots from Ariat have been designed with country life in mind. Still, you don’t have to be a tweed-wearing, sloe-gin drinking, Northumbrian gamekeeper to appreciate their many benefits.

Straight off the bat, these are some seriously comfortable boots. From the moment you slip them on the soft, spongy insole cradles your foot and the gusseted collar hugs your ankle. They’re also completely waterproof, which is great for stomping around in cowpats all day or, you know, just keeping dry when it rains.

Looks-wise, they’re not too shabby either. The waxy leather is soft to the touch and gives the impression that it’ll take on a nice patina with age. You could happily wear them with jeans at the weekend or even dress them up with smart-casual garb when the occasion calls for it.

All in all, a solid all-rounder of a boot that will suit those looking for a fuss-free daily driver that feels as good as it looks.

Dr Martens 1460 leather boot

The 1460 from Dr Martens sits alongside the best boots ever created in the pantheon of all-time footwear greats. This instantly recognisable British boot and has stomped its way through more than half a century, stopping off at countless subcultures along the way and becoming an icon in the process.

This is a boot we've had the chance to review long term and the first thing to say regards comfort. Dr Martens are famously unpleasant to break in. There's no getting away from that. It's an arduous and painful process that can last weeks depending on how often they're worn. However, once it's done, these boots will be the comfiest you've ever owned. You'll be able to walk for miles in them and that comfort will only improve with every additional wear.

In fact, comfort is this boot's biggest selling point. It's the cushioned sole that made it famous and is the reason it was born in the first place. It really is a pleasure to wear and we like the fact that it's such an intrinsic part of British counterculture. A boot with a story to tell.

Dr Martens fit true to size in our experience. However, they don't come in half sizes. If you're in between, opt for the next full size down.

Timberland 6in classic boot

How would you like to walk around with a piece of hip hop history strapped proudly to each foot? Well, you can. It's as easy as investing in a pair of Timberlands.

Timberland's classic 6in boot will never not be cool. It's long been a fixture of the rap music scene thanks to its chunky silhouette and vibrant yellow colour but it's about as practical as a boot gets too. It's fully waterproof, warm and very comfortable once worn in a bit.

Throw a grippy, commando sole into the mix and you've got a recipe for one of the coolest and most capable winter boots imaginable. Perfectly suited to tackling snow and rain, and maybe even protecting your toes from the occasional dropped mic at an underground rap battle every now and then.

The verdict: Men’s leather boots

One of the most frustrating things about buying leather boots is the breaking-in period. This wasn't an issue we experienced with the G.H. Bass camp moc ranger. The leather is soft, the sole is springy and they feel well worn in (almost) right out of the box. It's difficult to fault a good old Clarks wallabee too. For a suede option that's supremely comfortable, classic and stylish Clarks is the way to go.

IndyBest product reviews are unbiased, independent advice you can trust. On some occasions, we earn revenue if you click the links and buy the products, but we never allow this to bias our coverage. The reviews are compiled through a mix of expert opinion and real-world testing.