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With a good belt, and properly oversized shorts, you shouldn't have much trouble...
With shorts I wear a 1.5" tactical web belt. Infinitely adjustable. Appropriate match for shorts. Cheap.
My 5.11 belt cost me about $15. Works fine.

No problems carrying my HK .40 [P2KSK]
I do find that hitching my shorts just a bit higher helps too.

My problem is with shirts... Hard to find something light enough that still provides good cover.
Just ordered one of those Woolrich shirts... looking forward to giving it a try.
http://www.woolrichelitetactical.com/pr ... -shirt.htm" onclick="window.open(this.href);return false;
http://ep.yimg.com/ca/I/botach_2159_455710299" onclick="window.open(this.href);return false;