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 the one pictured here.