I, on occasion, carry an AMT Backup 380 in my front pocket. (no, lets not talk about the particular brand whether you like it or not, just the size and caliber). It is very easy to carry for certain scenarios. At 20 feet, I am extremely accurate with it. Doesn't require much aiming or anything. But a 380 out of that little thing is a monster. I can't even imagine how a 9mm would feel out of a gun that size. It would almost be unshootable
Now I know you mentioned that for a "pocket" gun, the 380 was fine, but if you were going to have a holster, then you should go up to the 9mm. There is a lot of logic to that. There are indeed 9mm pistols that mimic the size of 380's when it comes to the typical size used in a holster. Even the small ones. But it's still a matter of what a person feels most comfortable shooting. There's one person I know that ONLY shoots 45acp. He has a colt 1911A1 5", a short springer emp for carry, a sig p220, and a number of others. He thinks the 45acp is the BEST caliber against people and that's all there is to it. I don't even think he owns another pistol caliber. But I have to say, when it comes to the 45acp, I don't know anyone who is more proficient and knows more about a particular cartridge, than he is.
And there can definitely be others like that with the 380. Maybe they shot one, liked the feel of it, and that's the only caliber they shoot. They might have 2-3 different size pistols/capacities for different uses. And if that person really likes that caliber, and is really into it, then they are probably very proficient with it. As such, they are probably much better armed than the average person who shoots 2 times a year, and has a glock 17 with 15 rounds of 147 grain hollow points.
If a person thinks that another person is wrong in what they carry, because of the caliber or gun, then they are the one that is wrong. It doesn't matter if it's a 32, 380, 9mm mak, 9mm luger, 40sw, or 45acp. If the person is comfortable shooting their gun and caliber; and they practice and are proficient; then what more do you need. A 32acp can go up to 14 inches of penetration. Everyone says the FBI says you need a minimum of 12 inches. What's the problem. The 380 obviously can penetrate even more. If the person shooting is proficient enough to drop 3 round into the size of a baseball at 20-30 feet, and it's going to penetrate the minimum that the "Experts" suggest, then how can you say they are wrong.
I'll give some credit to those who criticize my opinion of the 32acp. Only because it's a slightly smaller diameter bullet. But the 380, 9mm, and 38 spl are all the same diameter bullet. And the energy in a bullet can't "Knock you down", so the only advantage of increased velocity and energy, is so it can expand the bullet; if it's a hollow point. And to be honest, the MAIN reason even for a hollow point, is to purposely SLOW down the bullet so it doesn't over penetrate. Yes, modern bullets also have the additional advantage of being able to create a virtual larger bullet diameter, and cause more damage, but that's a secondary purpose of the hollow point. If a person shoots a 380 in powerball, critical defense, or FMJ, and can penetrate 14-15 inches, how can you dog the caliber. That goes against all arguments for the caliber wars. Might as well just carry a 460. A 380, depending on the ammo, can penetrate anywhere from 10" to 17". So, what is so wrong with that???
http://www.goldenloki.com/ammo/gel/380acp/gel380acp.htm
I know there are some people that strictly believe in carrying the largest caliber that you can handle. That's fine and dandy. And if a person could ONLY afford 1 gun, then there is no doubt that I would recommend that they get a 9mm (If they just had to have a semi-auto) or a 357 magnum (If they could handle a revolver). The 9mm, while not a very versatile caliber, with only a few sizes; mainly 115, 124, and 147. (Yes, there are a few other unique brands). But the 9mm is very common in use, that it's availability and price is very good. If a person could handle the revolver, then the 357 magnum is the BEST ALL TIME ALL AROUND pistol there is. Everything from the 380 up to the 45acp and into the 357 magnum full loads into the 41 magnum. There is a round for EVERYTHING.
But in the "Better" world, people can have MORE than 1 pistol. If you can own more than one pistol, then there's nothing wrong with having different pistols and different calibers to take care of different scenarios. My AMT Backup 380 or my Walther PPK 32acp, both have scenarios in which they are BETTER than my Sig P220 45acp, my EMT, my Beretta 9mm, or even my cz-82 9mm mak. Now there are definitely times when the 32 and 380 aren't the best choice. But to say that they are never a good choice is silly.
Then again, there's the pessimists who insist that you "Never Know" what might happen. So you need to be prepared for the worst. Sorry, but I'm not buying it. You don't even believe that. If you really did, you'd never leave home. And if you did, you'd always be carrying a 44magnum or a shotgun. Because pistols by their very nature are a compromise. So there's definitely no way a 32 or 380 can handle all situations. But they are definitely adequate for certain scenarios. And for the person who only has one gun, get a 9mm or a 357 magnum.