6 Boots Every Man Should Own This Season

The tail-end of the year is a high-maintenance mistress to dress for, particularly when it comes to footwear. One miscalculated choice and that stride you stepped out of the house with soon turns into a squelch, dampening your overall style in the process.

Because no man should suffer a perpetual snail trail, make sure you’re prepared to ditch the trainers, park the drivers and lay off the loafers, it’s finally time to study up on the best boots for men this season.

6 Types Of Boots Every Man Should Own

Chelsea Boots

Boots Every Man Should Own, Best Boots for Men

Though popularised by rockstars during the Swinging Sixties, Chelsea boots had more regal beginnings – way back with Queen Victoria. Or more specifically, her royal shoemaker. J. Sparkes-Hall patented the slip-on design in 1851, and ma’am was said to wear them on the regular – be it horse riding or strolling through the palace grounds.

As a loyal subject, you might be more likely to traipse around beer gardens than Buckingham Palace, but this shoe’s core premise still stands: a simple design that’s as tough as old boots. Not to mention stylish.

“Try a real leather style in dark brown or black for optimal versatility,” says River Island head of personal shopping, Giles Farnham, who points out that – as with any skinned footwear – maintenance is essential. “Regular conditioning will ensure your boots age well,” he says.

The shiny stuff isn’t your only option. A pair in suede may require a more thorough assessment of the weather forecast before stepping outside, but they can help inject some texture into just about any look.

Desert Boots

Boots Every Man Should Own
Church’s Footwear

Like so many menswear classics – chinos, bomber jackets, nato watches – desert boots started out life serving, not on the front line of fashion, but in the military.

While stationed in Burma during WWII, British officer Nathan Clark noticed officers wearing shoes with suede uppers and a crepe rubber sole. On inspection, it was discovered that the footwear had been specially made in an Egyptian bazaar to withstand the tough climate, and clever Nathan, sensing a good idea, brought the idea home to the family business – British shoe giant Clarks.

The more casual variation of the chukka boot (which features a hard leather sole) is now a menswear staple, and while this material requires treatment with a weatherproof coating, they can power through most of what the autumn months throws at them. Aside from rain.

“Try your desert boots with smart denim,” says Chris Gove, creative director of British menswear brand Percival. “Perhaps indigo or raw selvedge, and complete with a crisp inch and a half turn up.”

Hiking Boots

Boots Every Man Should Own, Best Hiking Boots for Men
Church’s Footwear

No longer just standard issue for naturists, hiking boots have found a place on the fashion front row in recent seasons. But it was a rocky route.

Outdoor wear was considered niche apparel until boots brands like Carhartt WIP popularised the hunter-gatherer trend. From there, the likes of Hermès, Louis Vuitton and Bally followed, showcasing luxury takes on hiking boots that skyrocketed what was once a functional piece to the heights of high fashion. That said, they’re far more than a mere fad. Hiking boots were designed to face the elements paired with technical gear like men’s ski jackets and ski pants as well as cutting through the commuter mush.

When your kicks take a workwear edge, the go-to move is to steer your entire look into tougher territory. “Hardy footwear is best worn with equally hardy clothing, so try styling your boots with a rugged, heavy denim jacket and a chunky knitted cardigan,” says Farnham.

However, as rules around dressing relax, it’s also possible to pair more premium-looking versions with tailoring. Just be sure to opt for smart leather uppers, and match their weight with wool trousers as opposed to linen, or risk being banished into the menswear hinterlands.

Brogue Boots

Boots Every Man Should Own
Karsten Winegeart on Unsplash

The brogue has been a fixture of men’s wardrobes since the dawn of time (well, the 1900s at least), favored by farmers thanks to their decorative holes that act as escape valve for bog water. Equally, their high-ankled brethren, while a less traditional footwear option, are by no means less versatile.

In fact, there lies the brogues’ greatest strength. The addition of punched-hole detailing to a sturdy boot base guarantees a durable style that will sit well with both denim and tailoring.

“The traditional punch hole detailing means brogue boots look great with most things, but particularly heritage pieces like heavier wool blazers,” says Gove. “For extra points, take your trousers to a tailor and have them slightly cropped and tapered to highlight the boots.” As a general rule, the more holes on the shoe, the better.

Work Boots

Boots Every Man Should Own Sorel, Best Work Boots for Men
Sorel Footwear

If brogue boots champion Savile Row, then work boots skew closer to the building site. Which, in the modern-day, isn’t all brick dust, butt cracks and dog-eared issues of lads mags.

Thanks to the likes of Timberland, rugged work boots are hot property, with the brand having blown up thanks to hip-hop’s finest (Diddy, Kanye and Biggie have all sported their own pair in the past).

True, they may not sit well with suiting, but they are the perfect foundation to a jeans and T-shirt combo. (The same can’t be said for that hi-vis jacket, though.)

“As with hiking boots, keep your look rugged,” says Farnham. “A pair of work boots is your statement, so a white T-shirt, bomber jacket and grey marl sweatshirt will balance the look.”

Oxford Boots

Boots Every Man Should Own, Best Oxford Boots for Men
Myrqvist Shoes

Not all boots are five-pound clunkers replete with technical features and metal accents wrapped up in a Dales-ready design. For those that prefer a sartorial streak with what they put on their feet, there’s the Oxford boot.

Otherwise referred to as the ‘Balmoral’ (though technically this style is made using two different materials, such as leather and suede), this high-ankled shoe is the most natural fit for tailoring, owing to its smart closed-lace system.

“If your trousers have a break, it’s usually impossible to tell the difference between these and a standard pair of Oxfords, making them an ideal switch for winter,” says Gove.

That’s the risk of trench foot mitigated, then, now just to invest in a decent winter coat to avoid frostbite.

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