The Cowboy Boot (aka Western Boots)

5They’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.

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