The fewer the guns, the better
My primary gun is a Kimber Ultra Carry .45ACP in a Tucker Gunleather "The Answer" IWB holster.
I dress around the gun. Most of the time I wear dark slacks and an untucked camp shirt. The pistol disappears. Occassionally, I have to wear a coat and tie. Same rig.
If I have to go somewhere in shorts and a T-shirt (rare), then it's a S&W 642 in a pocket holster. I'm still in the process of picking out a suitable backup holster for carrying with the Kimber. May end up being an ankle rig.
Finally, on rare occassion I need to dress in such a way that neither the Kimber nor the 642 will do. That's when I carry my Colt Mustang Pocketlite in a SmartCarry.
In any case, I don't change from my primary unless I absolutely have to. None of this "what gun do I feel like carrying today?" for me. I know the limit of my skills.
I don't believe I'm capable enough to respond properly in the heat of the moment with anything but a 1911. I've been training with and carrying one for over 20 years. Hence the Mustang as a deep concealment piece. Same manual of arms, same immediate action drills, controls in the same place.
I chose the 642 as a BUG because it has the simplest controls of any J-frame. No exposed hammer, so no temptation/confusion over "should I fire single action or double?" I can shoot it with my weak (left) hand without gyrations over a safety.
The only reason I don't retire the Mustang completely in favor of the 642 is concealment. On my chubby, middle-aged body the flatness of the Mustang really helps.
YMMV one hell of a lot.
Bill