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. Definately 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....).