If you'll contact Kee Darnell with RM Holsters and try one of his Low Rider IWB holsters, I think it will be exactly what you're looking for.
866-288-9778
If you're going for deep concealment/pocket carry, I'll never understand the logic behind a tiny metal framed gun that weighs a pound like the P238 and micro Eagle. Kinda defeats the purpose IMO.
Ruger LCP for size but I find the 6 round capacity to be a negative. If you are set on it being a 380 but have a little flexibility, why hasn't anybody mentioned a Bersa? Good pistol for the $$$ (around $300+) and the CC version is smallish with an 8rd +1 capacity. Too small for my liking and I sold mine to get the regular Thunder. Eight round capacity (7+1), same low cost and a very good, reliable gun. Thumbs up for the Bersa.
Ruger LCP for size but I find the 6 round capacity to be a negative. If you are set on it being a 380 but have a little flexibility, why hasn't anybody mentioned a Bersa? Good pistol for the $$$ (around $300+) and the CC version is smallish with an 8rd +1 capacity. Too small for my liking and I sold mine to get the regular Thunder. Eight round capacity (7+1), same low cost and a very good, reliable gun. Thumbs up for the Bersa.
The OP asked about reliable pocket guns, the Bersas are neither.
Can't argue on the your "pocket" standpoint, but the Bersa I carry everyday and shoot regularly will disagree with your view of lacking reliability. It's not a Glock or M&P, but it has functioned flawlessly no matter what crap I've ran through it.
Check out the Beretta Cheetah. I don't carry but, I have the Ruger LCP and the Walther PK 380. The PK sucks. The Ruger is alright to shoot but, the Cheetah is the ticket in my limited .380 experience.