I typically carry, based off of season, attire, activity, etc, one of three pistols: S&W 642 in a front pocket holster; Kahr P9 in an ass pocket holster; 1911 Commander style (i have several) in a strong side hip holster. The pocket holsters I have modded slightly to ensure that they are as snug and properly oriented in their respective pocket. I also typically carry one reload in my weak side pocket. Spare mag for an autoloader, or a Speedstrip for the 642. If I need more ass to extract myself from the situation, there's always the bailout kit in my trunk.
I try to standardize what, how and where I carry as much as possible, which helps me in a few ways, not the least of which is keeping my strong hand free of relatively mundane, admin tasks.
In fact, the only real exception to my strong side, gun side philosophy is driving long distances, when I carry cross draw on my weak side hip.