I never carry two "on me" but occasionally have more than one with me.

I might bring several guns on out of town trips and switch them out according to dress and activity. For example, might pack an Airweight J Frame, a K Frame of some sort, and maybe a Glock or Smith Third Gen single stack in 9mm. Usually pack a few holsters....pocket, IWB, and OWB. Most often using the IWB.