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The biggest thing I would worry about is the holster and belt traveling up with the gun on a draw. I've done something like this for a rainy IDPA match, wearing rain pants with no belt loops. Of course, that was with a kydex holster and the tension screw turned down just for IDPA use, so things didn't really ride up. My OWB leather (a very nice Regulator by Nate!) grabs pretty well, and I can feel it pull on the waist of my pants when worn normally. Without belt loops to hold it down I don't think it would work the way you describe.
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“What is a moderate interpretation of [the Constitution]? Halfway between what it says and [...] what you want it to say?” —Justice Antonin Scalia
SIG: P220R SS Elite SAO, P220R SAO, P220R Carry SRT, P226, P239 (.40S&W), P2022 (.40S&W); GSR 5", P6.
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