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1. The Chelsea Boot (aka Dealer Boots)
A boot with an ankle-high height, a close fit and without laces. this boots employ an elastic panel known as goring, which allows the shoe to stretch when taking it on or off. Known and praised for its convenience.
How to wear them: Today, more refined varieties with dress shoe soles are making a comeback. 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.
2. The Chukka Boot (aka Turf Boots Or Bucks)
Like the Chelsea, the chukka boot 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.
3. 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. tips: 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.