For 10 years, I always wore my black ones in garrison, and jungle boots in the field. When I resigned my commission, I started working in an office where a lot of people wore cowboy boots with dress slacks. Since I was more of a paratrooper than a cowboy, I bought a pair of the brown ones and wear them regularly :-)
I wore my black ones while working for a EMS.Everyone wore Carolinas, but they looked cheap. The Real Jump boots were great because i have bad ankles and the support they had save me on a few occasions.
Never been into Cowboy boots...but then again in Pittsburgh,never really saw the need for them.