Winter boots are up there with big coats, cozy-boy jumpers and hot Ribena in the pantheon of cold-weather greats. They're practical. They're stylish. They're fun to stomp about in. Which makes them a must-buy once the temperature drops.
“If there is one item to invest in come winter, it should always be a pair of high quality boots,” says Mr Porter’s senior shoes buyer David Morris. “Not only are they 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.”
However, not all boots are made equal. For every Goodyear-welted outfit-enhancer, there's a pair made from plasticky leather that fall apart as soon as they step in a puddle. If you’re bored of squelching around in soggy socks at the first shower, then read on, and prepare to step into a more stylish winter.
What to look for in a pair of winter boots
Though the human race can knock out a new iPhone every year, 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 from the side, with recessed studs to help you keep your footing.
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 best men’s winter boot styles
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 is the work boot of choice for those.
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.
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, but if you want something winter-specific, then look for chunkier soles. Traditionally, Chelseas have been a sleek, fairly formal shoe, but brands like Prada and Church's have given them a bit of 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.
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 worn 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 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's obviously not the choice for winter, but you can wear leather chukkas exactly as you did your desert boots, back when it was dry. Look for a pair with two or three eyelets, cut from supple leather with a natural crepe sole (which, unlike boots with a Goodyear welt, can’t be replaced). Try a pair in classic brown which can be dressed down with denim or up with an unstructured suit.
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