Pocket carry? The tiny .380s all over the market lend themselves well to pocket-holsters, I have an LCP that lives in my pocket while at work.
I also opted for the 'older' LCP vs the LCPII or other .380s because of weight/size. The original is small and actually one of the lightest .380s, I think the P3AT from Kel Tec might be just barely lighter, so maybe look into that. Because if you are wearing lighter weight pants/shorts, having a big/heavy weight in your pocket can be somewhat noticeable..
It's also worth considering more 'slant' cut pockets on your pants/shorts, rather than 'U'/traditional cut jean front-pockets. This will allow for easier/fast draw, otherwise with typical jean pockets you do a sort of: "pinch, pull, grip, draw" technique. But everything is a compromise, I've never carried in a boot/ankle. If that's what you gotta do, then do it as well and efficiently as you can.