I actually thought this was pretty funny because my nephews are big in the cowboy look! The 10 year old is actually interested in horses (actually he said he prefers mules). The younger three (7,6, and 5), I'm not so sure, they liked to be lead on the pony when I had her, but never really showed an interest in 'learning' to ride. Two are very facinated w/ bulls, one wants to be a bull rider, although the other day he told me he wanted to get a bull and take it to the rodeo, I had to explain that the bulls are supplied, you don't bring your own.
Anyway why it was so funny, one of them has been abit intimidated by the big horse(s) (although he's getting over that) and told me one day he didn't want to 'be' a cowboy, he just wanted to dress like one! This was after sitting on the horse for a second, he got scared and wanted down.
As for how I feel about it, personally I don't think it would bother me, not sure I find the cowboy look 'attractive', it's not unattractive, but it's not something I really think about. Atleast this guy was honest, that's alot better then someone really playing it up and 'pretending'(that would bother me).