freeport,
I carry a Ruger LCP 380 with LaserMax. I have a custom made wallet holster by Uncle George (Austin, TX), that I carry in my back pocket like a wallet. I thought that it would be uncomfortable sitting on a gun, but you don't really sit on it because it higher on the hip.
I also have a Bersa 380 Thunder which is what I used for qualifying for my CCW. It's a great gun and a nearly identical copy of the Walther PPK (what James Bond carried...LOL)
In addition I have a small Jennings J-22, which is even smaller than the LCP. Yes, the Jennings is a cheap, unreliable, and inaccurate gun. But if you put about 250 rounds through the barrel to break it in, it becomes more reliable. Accuracy within 20 yards is good since that is where you are most likely to have to use it. I use CCI Mini-Mag hollow point ammo, which packs a pretty good punch for a 22LR.
I have now been looking at the Beretta Pico 380 and the Beretta Nano 9mm. Both are only slighly larger than the LCP but a very thin flat profiles...which is a plus for concealed carry.
Another factor to consider is the ammo. Sometimes ammo in certain calibers can be very difficult to find. With the popularity of small CCW guns, 380, 9mm, and 40 cal are often out of stock. This seems to be a bigger problem with the 380. Some ammo manufacturers only make one run of 380 ammo for the whole year. That leads to some people hoarding ammo, which quickly sells out and you have to wait months to buy ammo.
If you do not already have your CCW license yet, check your state laws since some require that you carry the same type of weapon that you qualified with...ie: If you qualified with a revolver, you can only carry a revolver, and if you qualified with an automatic, you may carry either a revolver or an automatic (that's how Texas CCW license works)
...Rich