How to wear them - Motorcycle Boot

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. Hells 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.

How to wear them - Hiking Boot

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 sweater in Fair Isle.

How to wear them - Cowboy Boot

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.

How to wear Chukka Boot

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 stop 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.

How To Wear Chelsea Boot

The Chelsea Boot (aka dealer boots)
Characterized by ankle-high height, a close fit and, most notably, no laces. Instead, the Chelsea boot employs 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 these pictured here.