Ah, the perfect pair of puddle-destroying men’s winter boots. There’s nothing better than rugged footwear that fits like the cobbler is still sewing in the sole. Stylish, comfy and hard-wearing; the dream combo for the best winter boot. But to achieve this, you need to know what you’re getting yourself into because you can’t just pick any old boot and expect it to be dreamy. The chunky boot is an integral part of the menswear survival kit and one to be taken seriously.
“Not only are they one of the easiest pieces to incorporate into a man’s winter wardrobe,” says Mr Porter’s senior shoes buyer David Morris, “they are also extremely comfortable, and offer great support and warmth during the cold and unpredictable months.”
Any source of support and comfort in the cold and unpredictable months is something to cherish, and the array of boots which have stomped into the menswear world over the last decade is dizzying. We’ve had the euro-hikers zipping up their North Face puffer jackets and lacing up technical boots that could scale the Eiger, right after they’ve done the Thursday night bottle shop run. We’ve had the shearling boom, the second – or possibly third – coming of the Hunter welly, the post-Lil Nas X yee-haw neon-Western reboot. And all the while, the old faithfuls – the Redwings, the brogue-boots, the chukkas – have stayed as reliable as ever.
However, not all boots are created equal. For every Goodyear-welted outfit-enhancer, there’s a pair made from plasticky leather that falls apart easily. If you’re bored of squelching around in soggy socks every time it so much as drizzles, then read on, and prepare to step out in style.
These are the best men’s boots of 2023
What to look for in a pair of men’s boots
A chunky boot can be the life raft in your morning commute when the puddles are deep, the snow is slushy and it’s too late to turn back. The criteria for cold-weather boots is different to the sleeker styles you wore all summer (your Chelseas, your chukkas, your deserts et al). Forget sleek, narrow silhouettes, look past fine suede and supple Italian leather, and opt instead for something that summons adjectives like, “chunky”, “hefty”, “shit-kicking” etc.
Though the human race can knock out a new iPhone every 12 months, the tech that keeps our feet warm and dry has gone largely unchanged for 5,000 years. “I would always recommend boots with leather uppers,” says Neil Kirkby, from heritage shoemaker Cheaney. “The natural material adapts to the shape of your feet with each wear, making them extremely comfortable for the long term, and when looked after properly can endure many seasons to come.”
Like most things in life, you get what you pay for when it comes to leather. The gold standard is full-grain leather, which can often be identified by a pebbly, textured finish. As the name suggests, full-grain uses the complete skin (cheaper leathers will often have been sanded down to remove imperfections) and as a result is stronger and more water-resistant.
Not only are boots one of the easiest pieces to incorporate into a man’s winter wardrobe, they are also extremely comfortable, and offer great support and warmth during the cold and unpredictable months.
When it comes to the soles, though, you’ll want something a little more substantial. “If the boot will be worn outdoors, especially in wet weather, avoid leather soles,” says Kirkby. Rubber’s generally your best bet, but that doesn’t only mean chunky commando soles (although they are great). If you’re after a smarter silhouette, Kirkby recommends Dainite soles, which have a thin strip of rubber that’s indistinguishable from leather to the casual observer, so still looks smart enough to wear with, say, tailored trousers. On the pavement-side, they’ve got recessed studs, which will keep you upright even when things are treacherous underfoot.
The final part of the puzzle is construction. A reliable pair of boots is more than the sum of its parts: how they’re put together is as important if you want them to last. “A Goodyear welt is often quoted as the hallmark of well-made shoe, and is worth the extra investment,” says Morris. Named after its inventor, Charles Goodyear Jr, the welt is a strip of leather which holds the upper, inner and outer sole together. When the soles wear down, you can cut into the welt and replace them without damaging the other parts of your boot.
“Not only is Goodyear worthwhile, I would argue it is essential,” says Morris. “How often have you found your perfect boot and then it wears out much sooner than you anticipated? Goodyear-welting ensures repair and refurbishments are possible, prolonging the overall lifespan.”
The essential men’s boot styles for 2023
Work boots were once what you wore on a building site or down a mine; now, they’re the footwear of choice for men who work in ad agencies. Which is strange, but good, because luxury brands have started to put their spin on the silhouette and you don’t really want to ruin your Cucinelli work boots by dropping a girder on them.
In any case, we’re talking about rugged, stompy boots with a hefty upper, padded collars (the part that wraps around the ankle) and a chunky sole, for protecting your feet from wayward nails or, in your case, really big puddles. Brown Timberlands are classic (and Drake-approved), but if your style leans more selvedge-and-flannel than Wu Tang hoodie, then Red Wing’s Classic Moc should be the work boot of choice.
Proper, heading-up-the-Matterhorn hiking boots are overkill for those of us whose idea of the great outdoors is an afternoon spent in a beer garden. But in recent years, they’ve crept into the mainstream thanks to the rise of sensible, utilitarian fashion. Now, this categorically does not mean actual hiking boots, which tend to be made from day-glo nylon and, while wonderful when you’re tramping up the Eiger, don’t look quite as good with a suit.
The better option is hiking boots like those from Italian brand Moncler, which blend functional details like hook eyelets with premium finishes, like pebble-grain leather or, if you’re feeling particularly cosy, shearling linings. Think of them as a wintry spin on the dad sneaker, with a bulky shape that works well with similarly rugged wares, like cargo pants and chunky knitwear. Basically, if they look like you could actually wear them up in mountain more recently than 1952, move on.
Unsurprisingly for shoes that have been a favourite of everyone from punks to royalty, Chelsea boots are among the most versatile boots in your rotation. The slip-on design dates back to the 19th century, when they were created by Queen Victoria’s shoemaker, J Sparkes-Hall, as an alternative to lace-up riding boots. Today’s Chelsea boots are more likely to be found underneath office desks or pub tables, and worn with everything from slim-fit tailoring to smart, rolled-up denim.
The best Chelsea boots work year-round – just go for chunkier soles in the winter and something sleeker and slimmer when things start to warm up. Traditionally, Chelseas have been a fairly formal shoe, but brands like Prada and Blundstone – the latter now available in new Kensington concept store One-ABP – have given them a rugged makeover of late, which means you don’t need to worry about the weather forecast before you slip them on. That said, if your style leans more traditional, then a slimmer-soled pair will dress up with a suit, or down with denim.
Brogues have been a smart-casual staple since the Thirties, when they were popularised by the OG royal style icon (sorry, Charles), the Duke of Windsor, then the Prince of Wales. Before this, brogues had been worn mostly by Gaelic farmers, with the distinctive perforations acting as a release valve for bog water. Not very #fashion.
In modern times, these holes are purely decorative (as a rule of thumb, more holes equals more casual) but they give brogue boots a sense of heritage. As with almost all footwear, darker means smarter – black brogue boots are trickier to dress down, tan ones won’t dress all the way up. But that said, they’re generally a more versatile choice than dress boots, in the same way that brogued Derbies work with jeans in a way that shiny Oxfords can’t. For authenticity, look for a Goodyear-welted pair from a British shoemaker, like Cheaney or Grenson, then wear them with everything.
Combat boots are among the most durable shoes ever made, which is what you’d expect from a shoe that has its origins in the footwear favoured by Roman soldiers. Traditionally crafted from hardened, reinforced leather, these are boots made for fighting in – though in modern times, they also work pretty well for commuting, going out, or just popping down to the shops.
Their modern home is the moshpit, which is why rock-adjacent brands tend to produce the best versions. Saint Laurent’s are almost too pretty to scuff up (although we think they look even better with a few dings) and Givenchy has put a high-fashion spin on the kind of combat boots last seen on East German policemen. Although of course you could just go to the source and pick up a pair from your local surplus store.
Another style with big military energy, chukka boots were first popularised by British troops serving in India, with the name ‘chukka’ taken from the speedy games of polo which off-duty soldiers would play wearing suede ankle boots. A variant with a crepe rubber sole was adopted by troops serving in Egypt during World War II, notably Nathan Clark, who was part of the Clarks shoe dynasty. He came home and crafted a suede version – the desert boot – which quickly became ubiquitous.
Suede is a good choice in summer (less so when it’s hammering down) but you can wear leather chukkas in any conditions, all-year round, which is another reason to invest in a pair if you prefer not to have to think too hard about what to put in the morning (the other reason being that they go with literally everything in your wardrobe). Look for a pair with two or three eyelets, cut from supple leather with a natural crepe sole – it’s grippy, lightweight and traditional. Try a pair in classic brown, which can be dressed down with denim or up with an unstructured suit. If you are concerned about being caught wearing them in the next beast from the east, consider protecting them with leather protector for that extra peace of mind.
Ushered into the mainstream by the first Duke of Wellington, Arthur Wellesley, in the 19th century, the Wellington boot has been a popular footwear option for a minute. And no matter your justification for investing in a pair – maybe you’re no stranger to a midwinter saunter through a National Trust, or perhaps you’re prone to jumping in muddy puddles à la Peppa – it’s certainly worth investing in some you can depend on ad infinitum.
Which pair, exactly? Well it depends. If you’re inclined to keep things classic, look to the British stalwart labels renowned for their takes on the waterproof shoe style – namely Hunter and Barbour. If, on the other hand, you’re a fiend for unorthodox takes on traditional menswear staples, it’s Balenciaga’s assemblage of wacky wellies (e.g. the Crocs x Balenciaga boot) that you should be heeding. And for those, like us, who want it all, a Wellington boot as hip as it is timeless, there’s the Bottega Veneta Puddle – a biodegradable stomper available in an array of colours.
Can we get a yee-haw for western boots? The silhouette had its genesis in the early 19th Century when bootmakers across Kansas, Texas and Oklahoma took inspiration from the Vaqueros (the OG cowboys of Spanish and Native American ancestry) to design a saddle-friendly boot that would protect the wearer from the threats of the wild, wild west. And although such styles are a lot more unnecessary some two centuries later, they’re still dangerously stylish.
Considering adding a rootin’-tootin’ western boot to your footwear rotation? Now’s a better time than ever as esteemed fashion houses such as Celine and Saint Laurent are getting into the cowboy groove. But one needn’t commit to spending a handsome ransom to do the hoedown throwdown – Ariat, Zalando and Soho Boots all stock reasonably-priced saloon-ready treads so that you may zig-zag ‘cross the floor on a budget.
We say sheepskin (or shearling) boots, you say Uggs – but, of course, not all Uggs are Uggs. Some Uggs are, in fact, Kenzos; others come from Suicoke. Regardless of their origins, they’re always cosy. It’s an incomparable feeling, submerging your feet into all that hide. A sensation that eclipses any stigma attached to the footwear style.
Needless to point out, Noughties nostalgia is responsible for the sudden ubiquitousness of said suede-shrouded stompers. And as the ladies look to Y2K queens Beyoncé and Paris Hilton for fluffy boot inspo, we look to the likes of Ben Affleck, Ronnie Wood and Orlando Bloom: carefree dressers who were donning Uggs et al. circa 2008, long before such shoes were cool. The consensus? The best way to rock a pair is to aim for an effortless look. Think baggy shirts layered atop white tees, loose grey joggers and a bedhead hairstyle. In other words, get dressed like you just don’t care – even if you care a lot.
While you’re here, why not check out the best menswear of the week.