Regarding the P&S, I had an S95 (which my 5-year old now uses), and have an S100. If you go that route, compare S100 vs. S110 pricing - they have the same sensor and lens, S110 only has slightly faster AF (still slow relative to your 60D), and the S110 *doesn't* have the ergonomic finger grip that makes the little S100 easier to hold.

I bought those two cameras because they had the largest sensor available in a camera that fits in a jeans pocket. That was before the Sony RX100 came out, and today I'd have opted for that due to the larger sensor size - a great little camera, budget permitting (it's not cheap).

But...do you need truly pocketable, or just small? If the latter is ok, consider the EOS M (if you're not in a rush, a new version is probably going to be announced relatively soon). With the 22mm pancake lens, it fits easily in a small belt pouch or coat/cargo pants pocket. Regular 18 MP APS-C sensor, IQ will match your 60D and the 22/2 is a very good lens. I picked up the kit at the $299 price a little while back, and I find myself reaching for that much more than the S100. You might set your 17-55 to 22mm for a while to see if a 22mm prime would work for you. The EF-M 18-55 IS is a pretty good lens, but IMO it eliminates the size advantage on the M + 22 setup.