The Best Men’s Footwear Styles You Should Know 2019

For many parts of your wardrobe, winter is the time to shine. We’re talking layering, reverse layering, chunky knits, and coats that mean business. A whole lot of ticks there, right?

One minor notch in the “eh, not so good” column is footwear. Winter really does scupper you. You become beholden to the elements. You rely on your smartphone’s inefficient weather app like a newborn fawn does its mother. But, in the immortal words of Tony Soprano, don’t let anyone make you feel like you don’t got options.

With that in mind, let’s take a look at autumn/winter 2015’s key footwear styles:

Vibram-Soled Smart Shoes

Italian firm Vibram started off making mountain boots, which is about as tough as tough shoes get. Spurred on by the unfortunate deaths of a group of mountaineering friends who perished with fingers pointed to inadequate footwear as the main assailant, the Italian brand’s namesake, founder Vitale Bramani, was inspired. He began developing a new rubber-based sole, eventually creating the first ‘lug’ sole, which replaced genuinely-quite-dangerous-when-icy leather hobnail shoes and changed the game in terms of grip.

While we’re not advocating you go rock climbing in them, Vibram has nailed heavy-duty formal footwear for those who need to traverse treacherous conditions to go and sit around in the office all day. Which is handy, because we’re unsure if there’s anything worse than falling flat on your arse in public.

Stylishness may vary wildly, but there are plenty of Vibram-soled options that run the full length of the formality spectrum: the dapper Dinkelacker Rio with its water-repellent brogue upper and Vibram Maximum sole; the super-luxe Visvim Black Patrician that looks like a Doc Marten on steroids; and Mark McNairy’s Country Brogue, which combines a traditional brown leather upper with a striking blue welt and contrasting white Vibram sole for the ultimate blend of classic and contemporary.

Of course, while Vibram is the original purveyor of rubber outsoles, every brand from high street to high-end now produces their own take, recognising the modern man’s desire for stylish and practical footwear. So, whether you’re a brogue, Derby or Oxford kind of guy, you’re sure to find something suitable on the current market.

Just think of all the bruised egos and arses saved.

Men's Vibram, Rubber, Commando, Lug Soled Shoes Outfit Inspiration Lookbook

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Leather Brogue Boots

With Red Wing’s ubiquity in many parts of the UK reaching Taylor Swiftian altitude, it’s time we considered branching out when it comes to boot styles. The brogue boot’s duality and durability mark it out as a key piece of cold-weather kit: perfect for grizzly pint-nights, a wet walk to work on chilly Monday mornings, or even dressing down your suit if your office is a little more left-leaning.

Mostly indebted to the old guard of British shoemakers, the fact that the brogue boot doesn’t look or feel like something cooked up by a demented army surplus store with a predilection for tortured foot-arches is only the half of it: they tend to be comparatively cheap, too. Clarks’ brilliantly monikered Montacute Lord boots clock in at just £90, while Bertie offers its chunky Cyrus boot in tan or black for around £115.

Of course, should the mood strike you, there’s always the option to take a deep breath and screen calls from your bank having coughed up a cool £395 for Grenson’s superb Triple Welt ‘Fred’ model – a style that is almost guaranteed to last a lifetime with proper care and maintenance.

The brogue boot’s outdoorsy roots makes them ideal for teaming with heritage cloths such as wool, cord and tweed, as well as dark denim – particularly if you opt for a rich chocolate brown or tan pair. Just remember to keep your legwear slim and tapered – not to labour the point, but just because they’re called ‘bootcut’ jeans, it doesn’t mean you should buy them. Nobody should buy bootcut jeans.

Men's Leather Brogue Boots Outfit Inspiration Lookbook

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(Single Or Double) Monk-Straps

Rest easy, denizens of #menswear forums of old, the faithful monk-strap remains a formal classic. Well, quite formal, anyway: you’re more likely to see them on the carefully unstructured, leather-skinned Sprezzatura boys of Italy’s smart-casual scene than in your office or at your common wedding, admittedly, but they’re still a purist’s choice.

Forget connotations of chanting men in ancient temples dressed in ochre robes and oxblood double-buckles – the monk-strap’s original purpose may have been to protect the feet of monks at work, but these days you’re more likely to find them on the FROW than a friar.

Traditionally, monk-straps sat somewhere between dressy and casual on the formality scale – not smart enough for suiting, but too dressy for a casual get-up. Now, though, you can easily team a pair with your tailoring. That said, your average off-the-peg, mid-range, slate-grey suit probably won’t cut the mustard with this one (dressier, often heavier suits, especially three-pieces, work better here), but you’re always welcome to try. As with anything: it’s the way you wear ’em, not what you wear.

Anyway, while the Italians (predictably) rule the roost – Giuseppe Zanotti has a mental gold and black shoe that’d make Liberace blush and Valentino does a pair that’ll make you believe in god – the rest of Europe is hanging tough, too. Footwear faithfuls like Grenson and Church’s have quality, understated offerings and Swedish shoemaker Vagabond is also in on the act, rounding off a very full field.

Men's Monk-Strap Shoes Outfit Inspiration Lookbook

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Leather Low-Top Sneakers

Never let it be said that sneakers – or trainers, if you’d forgive the apparently outdated nomenclature – are only summer-appropriate. While you’re best off boxing away pairs with delicate mesh insteps, leather variants prove hearty against even a British winter.

We aren’t talking the kind of soft leather you’d usually find on trainers, mind: that particular material will stand up against a quick sprinkling but a sustained splash will see their weight rise exponentially and, most importantly, totally ruin the finish. Thanks to the wonders of technology and clever coating, plenty of brands now offer styles that – while not all claiming to be ‘waterproof’ as such – are impressively water-resistant.

Adidas, as per usual, has the game on lock. Although some of the brand’s trendier options are made of too fine a leather to risk, its Superstars and Stan Smiths are pretty hard-wearing, meaning that they’ll see you right through the dark nights and still-quite-dark days of this season.

Nike, too, has plenty of leather options, including the Air Max 90s – which are trending so hard we’re a bit surprised they don’t yet have their own official hashtag. Oh, and Converse are offering leather Chuck Taylor All-Stars, too: perfect if you’re someone who still goes to college and carries their backpack over only one shoulder.

Men's Leather Low-Top Sneakers/Trainers Outfit Inspiration Lookbook

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Hiking Boots

Their benefits (stability, longevity) are clear but the thing with hiking boots is that they’re usually just straight up hideous. And not even cool hideous like the majority of Rick Owens’ gear. They’re ugly in a ‘really plain family from the Home Counties on the tube who all dress in shabby greens and brown with big rucksacks and faces that let you know that they secretly hate each other but are too dour and lonely to do much about it’ way. Quite a specific ugly, that.

But there are a few that really do look great by anyone’s estimations. Styles like Diemme’s handmade Roccia Vet boot are a real winner, being sturdy and made to meet the physical demands of a hike, but not forsaking sartorial touches like metal hardware, waxed laces and cow leather inners.

Other brands making boots built to last (and not to visually offend) include Timberland, O’Keeffe, Heschung, Fracap and Moncler. As a general rule of thumb, steer clear of styles whose majority surface area is made up of blinding bright neon hues and plump for something a little subtler instead.

Unlike your leather low-tops, a hiking boot should never get anywhere near your tailoring. This is a strictly casual silhouette, which will always look its best combined with equally rugged pieces – think thick flannel shirts teamed with heavyweight twill jackets and raw denim.

Men's Hiking Boots Outfit Inspiration Lookbook

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