How To Wear Men’s Boots
Think men’s boots are just for hoedowns and hiking? Think again. From Chelsea to chukka, there’s a whole wide world of options out there (even if you’re more the suit-and-tie type). So, buckle up, gents. It’s time to reboot your brain.
The Chelsea Boot (aka Dealer Boots)
Characterized by ankle-high height, a close fit and, most notably, no laces. Instead, the Chelsea bootemploys an elastic panel known as goring, which allows the shoe to stretch when taking it on or off. Although Chelsea boots rose to fame in the ’60s mod scene (the Beatles booted up in a similar eponymous style), the shoe first came into being over a century earlier during the Victorian era as a riding boot praised for its convenience.
How to wear them: Today, more refined varieties with dress shoe soles are making a comeback at the edgier end of Wall Street. We think it’s proof positive that suits and boots can live in perfect harmony — provided, of course, that the cut complements the Chelsea’s slim, sleek lines. Your shirt collar, tie and, yes, even your briefcase should have an equally trim proportion to the slimness of the boot. We recommend pairing your navy suit with brown Chelsea boots, like the one pictured here.
The Chukka Boot (aka Turf Boots or Bucks)
Like the Chelsea, the chukka is also known for hovering in the ankle area. But the similarities end there. This boot comes with two to three eyelets of lacing and is often outfitted in suede. In the 1940s, chukkas popped up as part of a trend toward casual dressing, and by 1950, the British brand Clarks had invented its iconic desert boots (essentially a chukka with a crepe rubber sole), solidifying the style’s spot in shoe history.
How to wear them: A recent resurgence in popularity has everyone from college kids to soccer dads sporting chukkas. And for good reason: It only takes a solid Oxford shirt and straight-leg jeans with a single cuff that gently covers the boot without breaking (so the pants fall straight over the shoe in a clean line) to do these shoes justice.
The Cowboy Boot (aka Western Boots)
They’re exactly as you imagine: A tall boot shaft at least above the middle of the calf, no laces and a heel of about two inches (known by footwear aficionados as a Cuban heel). Although similar riding boots have been part of an equestrian lifestyle for centuries, it wasn’t until the 1860s that decorative hallmarks like an angled heel and top stitching came into existence. They’re still the shoe standard with the cowboy contingent west of the Mississippi, but you don’t have to lasso livestock to own a pair.
How to wear them: For city folk, we suggest a more modern take in broken-in brown or tan with a rubber sole. And unless you can actually wrangle something, couple your cowboy kicks with jeans (preferably a dark and slim boot cut), an Oxford shirt and a tweed sportcoat.
The Hiking Boot
Hiking boots vary widely in appearance, but the key to sniffing out this shoe is a relatively rigid structure that provides support for the ankle without restricting movement. The first hiking boots were likely birthed in the 1870s in response to the emergence of mountain climbing as a sport in Europe, but it took over a century for the shoe to evolve into the all-purpose outdoor recreation hiking boot we recognize today. You’ll likely find a beat-up breed on the feet of the tree-hugging, granola-chomping set.
How to wear them: Fortunately, there are now more refined kinds that retain the function and feel of the original without the need for a fleece and a flashlight. Our take is best worn with rolled corduroys (a single cuff will do) and a shawl collar cardigan or fitted Fair Isle sweater.
The Motorcycle Boot (aka Engineer Boots)
The height ranges from above the ankle to below the knee, but all motorcycle boots boast a low heel in order to aid in putting the pedal to the metal, as well as heavy-duty leather for protection against an unplanned meeting with the pavement. Engineer boots are the archetypal old-school biking boot (as opposed to the tricked-out racing or motocross kinds) and are speculated to have surfaced during the Depression era when the Chippewa Shoe Company developed a boot based on those used for equestrian sports in England. Hell’s Angels and attorneys who attempt to ride their midlife-crisis Harleys are huge fans.
How to wear them: These days, you can flaunt a pair with all the elements of a true engineer boot without coming off like a costume. Toss them on in your downtime with a pair of black jeans, a relaxed-fit pocket tee and, of course, a leather jacket.
The Military Boot (aka Combat Boots)
As you might expect, boots made for the military are designed with one goal in mind: to shield you from an unfriendly environment. As a result, combat boots run the gamut from ankle-high to under-the-knee, and are typically made from technical materials like waterproof leather, Gore-Tex and rubber. The first boots for battle were worn by the Assyrian army as early as 1000 BC. Fast forward a few thousand years, and you’ll find them on the feet of everyone from generals to teenage gothic and grunge types.
How to wear them: Swapping traditional black boots for red ones and donning dark denim (complete with a couple of cuffs or tucked directly into the boot), a vintage tee and a tailored peacoat should keep you clear of counterculture territory.
The Winter Boot (aka Cold-Weather Boots)
This is perhaps the broadest boot group of boots, with styles from military-issue Kevlar lace-ups to suede and shearling-lined slip-ons. What they have in common? They all fit the foot snugly to help retain heat. Born from the simple need for survival, waterproof winter boots made of deer skin and tree bark with bearskin soles are at least 53 centuries old. And while structure and style have thankfully changed, the basic premise of protection against winter’s woes remains the same. No one north of Florida should be without a sturdy pair past December.
How to wear them: We’re currently occupied with technical takes that combine leather uppers with reinforced rubber on the toe. Trust us — they’re nothing short of genius for when snow turns to slush. The combination of materials also allows you to comfortably keep them on throughout the day with jeans, a thermal Henley and fitted puffer coat.
You don’t need to be braving the elements or hoofing around on horseback to buy into men’s boots. Turns out, even if you’re on desk duty, there’s still a way to slip ’em on with style.