Glock 26 or 27 are WAY out of the question in my opinion. I love my glock, but they are not pocket pistols. Sig p238 I also own and love, but again, not for pocket. if u have a hard time with carrying iwb, then odds r u don't have huge pockets. (Like me, I'm not a big guy and my clothes aren't baggy) the p238 fits in most medium to large pockets, but definitely prints, and the beaver tail snags for sure. my Kel Tec, well... I just wouldn't recommend after owning. nuf said there. I have heard of reliability issues with diamondbacks, and the 9mm is not .380 sized. I owned a Kahr pm9, but sold it. it was a great gun, but also a bit large for pocket carry. people said that was nearly .380 size also, but they were full of crap. the Kahr p380 is very significantly smaller than the pm9! looking at the numbers, it may not seem so, but hold them both and u will see what I mean. there's a big difference. I believe u will get that comparing any pocket .380 to their similar 9mm counterparts. that said, after my experience with my Kahr pm9, which was a great one, I will be picking up the Kahr p380 for my next pocket pistol. my pm9 shot great and was flawlessly reliable, just wasn't the size I wanted. so that's my recommendation.