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The Most Stylish College Basketball Coaches of All Time

  • Najib Benouar

Basketball Coaches

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.

On to the Sweet 16, where Cinderellas are made.

Wooden and Massimino(1) John Wooden’s Glasses vs. (16) Rollie Massimino’s Hair: John Wooden was legendary for many reasons (including being a Kempt Icon), but those thick-rimmed glasses are what made him instantly recognizable. Rollie Massimino’s calling card was that wildly unruly hair above an otherwise well-coifed getup. It’s a move that’s gained favor in corners of menswear and most corners of Brooklyn, but we’re not seeing an upset on this one.

Knight and Tarkanian(2) Bob Knight’s Red Sweater vs. (15) Jerry Tarkanian’s “Chew Towel”: The only thing more iconic about Bob Knight than his scowl is his red sweater. Tarkanian had the towel he incessantly chewed on during games. As far as iconic NCAA artifacts go, these are both museum worthy. But Knight has the edge since his item is actually a piece of clothing.

Williams and MacGee(3) Roy Williams’s Carolina Blue vs. (14) Herb Magee’s Mustache: Roy Williams somehow manages to get a splash of the Tar Heels’ blue into all of his kits—even when it’s a subtle windowpane over peak lapels (that’s really where he earned his high seed). A mustache can do wonders for a man’s persona, and Herb Magee has taught us that, but we're not sure that’s enough to topple Williams’s peak lapels.

Phelan and Carill(4) Jim Phelan’s Bow Tie vs. (13) Pete Carril’s Princeton Offense: We’re calling this one “The Battle of the Bow Ties,” and we may have our first upset. Two legendary coaches with legendary penchants for the trad neckwear. It’s close, but Carril’s doubling down on all things Ivy League (including making Princeton basketball relevant) gives him serious momentum. Has our Cinderella arrived?

Thompson and Naismith(5) John Thompson’s Towel and Glasses vs. (12) James Naismith’s “Teddy Roosevelt” Part: We’ve got to give this one to Thompson and the ever-present towel, ready to mop his brow. And to those wire-frame glasses, which could cut a stare that even kept Allen Iverson in line. But we can still admire the swashbuckling hair part of basketball’s founder.

K and Pitino(6) Coach K’s Look of Determination vs. (11) Rick Pitino’s Coke-White Suit: It’s hard to like either dog in this fight—you’ve got a Dukie and an indescribable commitment to white suiting. This one is going into triple-overtime, and ultimately, none of us win.

Carneseca and Sanderson(7) Lou Carnesecca’s Cosby Sweaters vs. (10) Wimp Sanderson’s Madras Blazers: We’re getting into the shake-up zone, and here’s one we weren’t sure on. Carnesecca was fond of the lumpy old-man sweater and wore it quite well, but Sanderson's combination of madras blazers and hilarious name could end in old Wimp hitting a game-winning buzzer beater.

Pearl and Chaney(8) Bruce Pearl’s Orange Blazer vs. (9) John Chaney’s Vestigan: Both men have committed to their look. On any given sideline, you’ll see either of them in their signature blazer or cardigan vest. We can’t knock Chaney’s understated stylishness here, but the commitment necessary for a blazer that outrageous commands some respect. (Similar to why the full-court press always wins.)

Tune back in tomorrow to see who makes it into the Elite Eight...


Today's winners in the Elite Eight.

The title contenders in the Final Four.

And the grand finale.