I regularly carry revovlers from the 70s, 80s, and 90s. Most of my regular carry guns fall on that spectrum. Sometimes carry a 1969 Colt Agent. That's probably the oldest in the carry rotation.
I have carried this before several times in my pocket. Also have carried it in a leather case. It is a Colt 1903 Hammer in .38 ACP. The .38 ACP is the forerunner of .38 Super. This is 1914 manufacture.