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Put your gun/holster rig on and anything else you plan to carry inside the waistband (an IWB magazine holster?), then thread the string or measuring tape through your belt loops and over your holster etc. Pull TIGHT. Mark the string/tape. This is the approximate lenght of belt you'll need (perhaps even an inch larger just in case.
Various custom belt makers have their own similar instructions. Follow each manufacturers instructions when ordering their belt.
Recommendations:
USA1 is right to try a police supply store like Top Brass and pick out a 5.11 (or similar brand) "off-duty" or "concealed carry" belt that you can try on in the store. Buy it, wear it for a while, see how you like it. This may be all you ever need.
If you find yourself wanting more and/or better, then I highly recommend these two companies:
http://www.thebeltman.net" onclick="window.open(this.href);return false; - simply the finest leather concealed carry gun belt made. Period. Only belt I've ever used withOUT a plastic liner that is still stiff enough to hold up my handgun/holster rig all day
http://www.thewilderness.com" onclick="window.open(this.href);return false; - best military-style "web belt" I've tried so far. The "easy-fit" version really makes sizing much simpler. If you've got a bit of spare tire like me (OK, a spare tire holding up a water balloon
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http://www.thewilderness.com/storepinna ... t=142&pg=1" onclick="window.open(this.href);return false;