And make no mistake about it. Kent knows his way around all of the cowboy stuff. On one shopping trip, he had his eye on an exquisite cowboy hat.
"This hat is $5,000. It's made of chinchilla fur and has real diamonds on it," said Richard Alcala, storeowner.
It's a little steep, but this urban and urbane western wear fanatic knows he's come a long way from the days of the original black American cowboys.
"In the movies, you had Buck Jones and white guys on white horses, but you seldom saw a black cowboy," Kent said. "At the rodeos, if you get a chance to see a black rodeo, you would be thrilled. It is as fine of entertainment as you can imagine."
It was his famous DJ work that led directly to his love of the cowboy lifestyle. Several years ago, some guys came into a club in Harvey where he was spinning. They were wearing cowboy hats.
"I said, 'How much, $60?' They laughed and said, 'Try $300 or $400,'" Kent said. "I got interested and said, 'I got to get me a hat.' Then I bought some boots and then a horse."
He called the horse Dusty Stepper. He's still around, but his ailments make him unrideable these days. So to get his equestrian fix, Kent goes to the Silver Stallion Ranch outside Harvey, where the 81-year old gets his cowboy groove back.
"Maybe I'm not the best rider in the world, but you can tell i have ridden before. You just kind of get in with the horse. You go along with him and become one," Kent said.
He said it's the ranch where all the pressures of being a broadcasting legend, a hall-of-fame radio man and just being Chicago's Herb Kent seem to melt away.
"You might look relaxed, but you ain't relaxed," Kent said. "At the end of the day, you could be, 'Oh, I need to go someplace and get it back together, so this is good."