For a long time, . . . being a "good ol' boy" was decidedly better than being an effete urbanite, and Republicans liked this contrast. Times are changing. Republicans are running out of old, white, married, rural voters. Being a "cowboy conservative" ain't what it used to be. . . .
Younger, more diverse, and cosmopolitan voters aren't so much embracing liberalism as they are rejecting what might be described as a caricature of a Republican. It's an image, largely of Republicans' own creation, that repels these voters culturally and aesthetically. A 2014 survey of millennials, for example, demonstrated that "[o]ften, they decided they were liberals because they really didn’t like conservatives."
The stereotypes that George W. Bush helped cement about the "dumb" swaggering cowboy made it almost impossible for Rick Perry to reinvent himself. The two men were never particularly close, but the prospect of electing another Texas governor (literally, the next Texas governor after Bush) was always going to be a tough sell, especially since the two were stylistically very similar. Bush left office extremely unpopular, and didn't just damage the Republican brand; he did specific damage to a particular type of Republican. . . .
In the end, Perry's accent and swagger were too much a part of our collective conscience for even hipster glasses to overcome.