Introducing Kempt’s March Madness bracket, wherein we pit the most iconic college basketball coaches against one another in an attempt to finally nail down who’s the most stylish of them all.
As you’d expect, it takes more than just sporting a pocket square or one nice blazer every so often to be named one of the most stylish college coaches of all time—everyone looks at least halfway decent in a suit and tie.
We were looking for coaches with a distinct through-line of personal style—and since most of these guys spent decades and multiple trend cycles on the sidelines, it usually came down to one iconic item they’d never given up. John Wooden’s thick-rimmed glasses, Bob Knight’s red sweaters or even Jerry Tarkanian’s “chew towel”—that sort of thing. Even if the pattern or cut of their sport jacket changed, that item didn’t. Which meant a guy like Jim Boeheim just missed the cut, because you might not even recognize his surgeon-cuffed look of today as the same guy who wore this in the 1970s. (Also just missing the cut: Gary Williams and his signature sweatiness.)
But there were plenty to choose from, and we just managed to cut the field down to the Sweet 16—which is where we’ll begin today, and continue to narrow down as the week progresses.