I agree with T_Y that it depends somewhat on the type of pants/shorts you're wearing. However, I pretty much draw the line at 2- to 3-layers going into my pockets, especially after getting the "are you just glad to see me" line from a friend when pocket carrying a Deluxe Tinker 20 years ago. Since then, anything larger than the SuperTinker or Yeoman goes into a sheath.
Here's a picture I just shared in a thread on Cybertools. I use the Zermat sheaths for the most part, using the Med for 3- to 4-layers and the Lrg for anything larger. I do have an older nylon horizontal belt sheath (Belt Hugger) that I like even for the Yeoman. It's much more unobtrusive visually and less constrictive.