My husband rode before I met him. He didn't own a horse, but he did ride others to work cows and had done so for some time. When we first met, I was still in college and renting a tiny place with 2 stalls, I had my gelding that I had for years and one "fixer-upper" horse that was a project. Of course, money was tight, but I had my horses and my dog, so life was good. I remember the first week that we were together, most guys brought me flowers, he showed up with some nice hay in his truck. Definitely better than flowers!
I knew plenty of K-Mart cowboys, my rule was always that if my horse didn't like you, you were out. He always could pick out the losers. Honestly, most of the cowboys that I know only look the part when they are actually using it. Even then, a lot of them are in baseball hats.
I wouldn't consider myself in the "cowboy" class at all... sure, I wear wranglers and boots every day, and increasingly "button up shirts," however, it's usually a dirty ole cap. Got the "cowboy hats" but they're all too clean, usually only bust out with them for some sort of "special occasion," or if I happen to be working a job dealing with cattle regularly. I did that for a while til I started picking cotton 60 miles closer to my house.
It's kind of funny because I was the one who had the horse when I met my wife. And he took to her just fine, and I actually spent a LOT of time on her old gray horse before she got to call him officially "hers." sad for her, however I knew I liked him and he'd be ok for her. Hell, I bought her the old dodge she's got (because "I HAVE TO HAVE A TRUCK!!!" even when it cost twice as much to drive? "YEEEEEEES, I DON'T CAAAAAARE!!!" ok, not QUITE like that, but it's the idea....).