I normally carry Zero guns. My wife forbids me from owning guns. I do shoot and have a CHL.
Occasionally, when I go fishing or shooting with my dad, he'll loan me one of his guns. A 380 such as a Ruger LCP or a Kel-Tec P3AT is perfect for winter because it can fit in a coat pocket. You can draw from the coat pocket while driving with a seat belt on. You can put your hand in your pocket when there is a perceived high threat level. It reduces draw time when you already have your hand on your gun.
In the summer, carrying a Glock 19 in a Smartcarry is perfect. With a Smartcarry, you can wear shorts and still carry a full size service pistol. It is a slow and awkward draw in the car with seatbelt on, but it is possible. I can see it being fast with practice.
If the threat level is high such as using an ATM at night or one of those Redbox DVD rental machines in front of the convenience store at night, then I'll carry 2 guns. Why 2 guns? Guns are mechanical and may fail. It is faster to grab a small gun instead of a spare mag if you run out of ammo. Plus, modern mouse guns are no bigger than a spare mag (almost).