The accusation, now frequently heard, of “cowboy politics” stems from the iconic image of Ronald Reagan as an all-American denim-clad horseman. But it turns out that, while Reagan had long enjoyed riding horses, his cowboy attire originated as a bit of showmanship:
In 1966, a local reporter from KTIX in San Francisco wanted to do a segment on horseback with the candidate for governor of California. Lyn Nofziger, Mr. Reagan’s press secretary, accompanied the reporter and was shocked to see his candidate in jaspers [jodphurs?] and English riding boots.
“When he changed into his riding clothes, he came out. And I looked at him—and he was not yet the governor—and I said, ‘You can’t do that,’” Mr. Nofziger recalled. “He said, ‘This is the way I always ride.’ I said, ‘This is not the purpose of that. It’s to get votes. They’re going to think you look like a sissy!’ He’s a great cowboy, looking at him. He played a cowboy in movies.
You can find photos of Reagan in his more aristocratic, English riding-wear here.