I wear dress cowboy boots to work almost all the time, with suits and with sport coats, and with slacks and ties. I am required to wear a tie, and I alternate traditional neckties with bolos and western ribbon ties. I wear a Stetson in the winter and a Bailey Panama in the hot weather (Well, OK, I wear the OR Sitka Sombrero in the rain...). I have had only complements on my boots and the Stetson. Ditto the bolos. One day, I was at a meeting wearing a "normal" necktie. A guy from the HR Center said "Wow! You have a regular tie today. I like your bolos, but I wouldn't have the cajones to wear one." I couldn't think of anything smart to say in reply, so I just said "Well, I wear mine around my neck."

Bottom line: Wear what you want, as long as it fits into your work situation. Outside of work, you are free to wear whatever suits you. Part of "what suits you" is your perception of what your social groups will view as favorable. I plan to ease into work with business kilt attire a day or so per month. If anybody gives me any static about it, I can always say that I moved to the kilt because they didn't approve of the cowboy boots, bolos, and hats.

Who gives a carp about what THEY think? It's all fun, anyway...