They are cut to allow clothes under the jacket for cool weather construction or outdoor work. You can usually fit a jacket underneath the Carhartt at the same size.
Colorado Springs? Depends on how much work outside you do, how much wind you have to put up with, and how you normally dress when you do, but I would suspect you want a Jacket that fits rather than one that goes over another jacket which is what you want when the temps are cold (0F and below).
Remember you can always dress warmer (put a vest over your jacket, add various kinds of warm underwear, etc) but you don't want to be sweating when you are going about ordinary daily tasks.