The 14 best men’s boots for winter, from chelseas and lace-ups to wellies

I haven’t always worn boots. For years I wrote them off – at 5ft 8in, I was convinced anything above the ankle would make my legs look shorter. Then I started wearing them with the right trousers – a straight leg that falls over the top – and realised I’d spent a decade getting winter wrong. All anyone sees is a smart pair of shoes that happens to keep your ankles warm.

Here’s the thing: boots needn’t be intimidating. They’re just the wintry version of the leather shoes you already own. A chelsea is your loafer – it goes with pretty much everything in your wardrobe and every event in your diary, Christmas parties included. A derby boot is laced up, a bit sturdier and just as happy with jeans. The chukka is your weekend trainer. And the chunky, rubber-soled ones? Just think of them as an umbrella for your feet.

Whatever you go for, my advice stays the same: keep it classic. Trend-led boots tend to look tired by the following winter, whereas a well-made, time-tested silhouette in full-grain leather will see you through years of wear. And if you want to know whether a pair is worth the money, flip it over. A stitched-on sole (look for “Goodyear welted”) means a solid structure, and, most importantly, that a cobbler can put a fresh sole on when the original wears out.

These are the 14 best you can buy now, from high-street stores to heritage footwear experts.

The best men’s boots for winter

Best for winter in the city

Barbour chukka boots

Barbour has spent more than a century dressing people for the outdoors, so it makes sense that its boots are just as tough as its jackets. I’d recommend these for anyone who wants a single pair that does everything. A boardroom meeting; drinks after work; a muddy trail walk: these boots can handle plenty of winter outings. Now all you need is the wax jacket.

Best value lace-ups

M&S leather boots

Marks & Spencer menswear just keeps getting better. Just look at its London fashion week runway debut in September: Kit Butler walked the Design museum runway in a proper rain mac with stylish straight-leg jeans, while Lennon Gallagher’s grey suit and tonal knit would give Savile Row a run for its money. Not bad from the place you buy Colin the Caterpillar. These Autograph (M&S’s upmarket line) lace-ups are another example: they’re the kind of boots you’d expect on your well-dressed uncle, whether with jeans at the pub or chinos on Christmas Day. And they’ll only look even better a few winters in.

Best high-street chelseas

Schuh Dice boots

Schuh is hard to beat for high-street footwear, especially chelsea boots. These tick a lot of boxes: all the smartness of a chelsea, a rubber sole that can handle a slippy pavement, and real leather. If you’re shopping on a budget, the material is a corner you really shouldn’t cut. Synthetic uppers tend to crack and wear much faster than leather, and once they go, there’s no saving them.

Best counterculture boots

Dr Martens 1460 Ambassador

Everyone knows the yellow stitching. It’s Dr Martens’ calling card, often spotted on the kind of guy who knows the bouncer at every gig in Camden. The OG is the 1460, an eight-eye boot that’s barely changed since the 60s and has been through everything from punk and ska to Britpop and grunge. The catch has always been the break-in period – but these bypass that, made from a tumbled leather that feels worn-in from the box. It’s probably best to keep some Compeed blister plasters on you anyway, just in case.

Best for Scandi minimalism

Brian boots

Good-quality, no-fuss footwear is Vagabond’s MO. It sells all the staples in shades of dark brown and black, with clean lines and zero (noticeable) logos. Suede is where the brand shines. These are the colour of a good espresso – and they’ll make a pair of indigo jeans and a chunky knit look like an outfit you’ve spent time thinking about. They’re also so light you’ll barely notice you’re wearing boots at all – just give them a spray of suede protector before you let them loose.

Best heritage zip-up boots

Grenson Richie

Yes, Grenson is on the more expensive side, but you really can’t fault the quality. It’s where almost all of my favourite leather shoes come from, and they’ve all lasted for years without needing repairs. These are my pick this season – an understated zip-up with a wide, flat toe that sits nicely under straight-leg jeans or work trousers. And because the sole is Goodyear welted (stitched rather than glued), when you do wear them down, you can send them back to Grenson’s Northamptonshire factory to be resoled for a fee.

Best budget zip-ups

Asos leather boots

If you like the look of the Grensons but not the price, Asos has an affordable alternative. These are the same sleek zip-up idea, and they’re real leather too. Unlike the Grensons, though, they’re not Goodyear welted, so it’s unlikely they’ll last you a lifetime. They may last a few seasons, but a pair you can properly resole is usually best in the long run.

Best wellies

Muck Boot Woodland Pro

Living in London, I don’t have much use for wellies. My dad, on the other hand, does. He lives in the Forest of Dean, so we’re talking two dog walks a day through muddy woodland, often in the rain. Since swapping his Hunters for Muck Boots, he hasn’t stopped going on about them: warm feet when it’s frosty, cushioning that makes them feel more like trainers, and an adjustable calf that allows space for trousers – basically, in his eyes, they can do no wrong. Hunter will always be the stylish choice, but for practicality, Muck Boots clearly take gold.

Best for coastal walks

Blundstone x Finisterre lace-up boots

Blundstone has become something of a national treasure, despite its Australian roots: the original chelsea has gone from Tasmania to just about every festival field and school run across the UK. For something fresh, though, you could try the new collab with Cornish brand Finisterre. It’s a lace-up in dark brown waxed suede, well suited to brisk clifftop walks, as well as the lunch reservation that follows. Best of all, they feel far more stylish than most walking boots, so nobody will mistake you for someone who’s about to take on the Pennines.

Best statement boots

Camper Dean

If you know Camper, you probably know it for its playful side – most of the collection looks like it could’ve wandered out of a cartoon. My favourite pair right now, though, is actually fairly normal – at least at first glance. It’s a suede chukka, just scaled up, with a structured upper, a rounder toe and a thick black sole that gives it some heft. So, if colour isn’t your thing, let shape do the heavy lifting.

Best derby boots

NPS walnut brown calf

You might not know NPS from the name, but you’ll almost certainly be familiar with its history. The company has been making boots in Northamptonshire since 1881 – and, for 35 years, it made Dr Martens under licence. These days, though, it makes boots under its own labels, including the better-known Solovair (a portmanteau of sole of air). These derby boots are classics from the NPS Heritage line: they could take you from a book launch in Bloomsbury to a farm shop in Suffolk and dinner at a fancy restaurant without an outfit change. They’re Goodyear welted, too, so they can be resoled rather than replaced.

Best cult classic

Clarks Walla Orkhon

The Wallabee has had more lives than most cats. It went from 60s counterculture to Wu-Tang Clan, who essentially wore them as a uniform, and it’s been a go-to for insider menswear nerds ever since. Purists might argue the OG is barely a boot, but this new winter-ready version settles the debate: it keeps the moccasin upper but now sits on a chunky sole, and swaps the delicate suede for a hardy leather. The cherry brown is a considered finish among a sea of chocolate and black.

Best smart chelseas

Cos leather boots

Every man needs one pair of boots that can stand in for smart shoes at formal events. This is it: Cos’s slim chelsea with a flat, barely there sole that’s a sophisticated match for tailoring or smart trousers. Unlike most formal boots, which come on slippery leather soles, these have rubber underfoot, meaning you can leave the function with your dignity intact – no matter how many times you visit the free bar.

Best oxblood boots

Timberland Premium 6-Inch

Few boots have a CV quite like Timberland’s six-inchers. They started out on building sites in the 70s – where they’re still very much a workwear staple – before being adopted by the hip-hop scene in the 90s (Biggie name-checked them so often that the brand eventually released a tribute pair). But you don’t need to wear them with baggy jeans in 2026: this burgundy version is a grown-up take that lends itself to anything from dark denim to black trousers. They’re also waterproof and insulated, so should see you through the wet and cold months of winter.

For more, read our roundup of the best men’s coats for autumn and winter