As far as jeans go, it's a mixed bag. The issue is that the pockets usually aren't deep enough. It's a two-fold problem: one, the longer items (like my ASP key defender and Clinch Pick) stick out the top of the pocket, and two the shield itself will print along the bottom lip because I'm trying to keep as much of the spray/CP covered as possible. Having said that, when using it with just a folder and light clipped to it (or even a PPS mag), the second problem goes away because it doesn't need to be stuffed down as deep. It worked very well, for example, with my FourSevens Quark and a Spyderco Endura.
Slacks on the other hand work very well once the thing's broken in. I have two, one for my LH pocket that'll carry pepper spray and a Foursevens light and one for my RH pocket set up for a Clinch Pick. The LH shield stays with me regardless of what I'm wearing.
Jesus paid a debt he did not owe,
Because I owed a debt I could not pay.
Get some of those Blue Force Gear Ten Speed pistol mag pouches. They'll hold all sorts of stuff -- lights, mags, folding knives, pepper spray, etc.
Here's what I've settled on for my LH pocket setup:
I'll usually just move the light into the mag pouch if I'm not carrying a PPS that day. The RH one is just the stock Clinch Pick sheath and nothing else, tweaked to where it works with my slacks.
Ok, I'll bite.
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It nestles into the utility pockets of my carhartts. SOFTTW on one side, tiny kit on the other.
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I <3 Caboose's Med Kit and Trimmed CP sheath. Have you tried the tek-lok with the opening going up? I found it is easier to put on and take off that way.