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An UrbanDaddy Publication

Icon: Amarillo Slim

  • Najib Benouar

Before all the bright lights and legitimate businessmen showed up, the gambling scene was dominated by a handful of flamboyant and mostly unsavory characters. The face of that scene: a cantankerous Texan by the name of Thomas “Amarillo Slim” Preston, who lost his battle with cancer just last week. He was a pool shark, a rounder, a proposition bettor, a bookie and a four-time WSOP champ.

The man would wager on anything and stack the odds in his favor whenever possible—he once talked a Wimbledon champ into a one-on-one tennis match, then insisted they use skillets instead of racquets (and won). He played poker with the likes of LBJ, Nixon and Pablo Escobar. He wore a ten-gallon Stetson with everything. He was a recurring Johnny Carson guest. And along the way, he took gambling from its smoky backroom roots to the mainstream. (It’s no coincidence that the most televised and popular form of poker today is his beloved Texas Hold’em.)

Here’s a look back at some iconic photos of the gambler in the ten-gallon hat.»

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One Hat at a Time


Here’s a late-breaking addition to yesterday’s winter hat compendium: our favorite southern gentleman Billy Reid has thrown his cap into the ring, in the form of a collaboration with the fedora godfathers at Stetson.

This one is our favorite, but there’s plenty of more wintry models to be found, including a pair of sharp driving caps and an achingly handsome cordovan aviator. It’s the kind of classic gear you expect from Stetson, given a modern brush-up and a bit of swamp-friendly flavor by Mr. Reid. It’s tough to go wrong with any of these—even if you’re more interested in warmth than style.

We didn’t even know they had winter in Alabama…