Dressing Around The Gun
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First off, let me say that I favor Inside The Waistband Carry.
With that in mind, I select my clothing with an eye towards concealment. My pants are 1"-2" larger in the waist than if I didn't carry a gun. My "cover shirts" are cut roomy, or in the case of T-Shirts, one size too large. I like dark colors and bold patterns to help disguise the gun I'm trying to hide, think Hawaiian here. My suits are gut to accomodate the gun in my pants and one in the pocket. Pleated pants work very well to hide a gun.
In the summer I wear Cargo Shorts and an untucked Hawaiian shirt with a T-Shirt underneath. The "covershirt" hides my 4" N-Frame Revolver or my Glock 19 with no problems. In the weakside pocket is my BUG. In the winter people say it's easier to hide a bigger gun. Maybe so, but if you pay some attention to your clothing you can hide that same gun most likely in the summer too.
I demand high quality holsters and belts. There is no sense in spending good money on an exspensive holster only to mate it with a cheap belt. That's like breeding a prize winning cutting horse mare to "Tony The Wonder Pony" from the circus.
For where I live I do not look out of place. No Trenchcoats in July. I'm not a "fashion plate" but I do look respectable and acceptable wherever I go. Case in point, I went to a party, could only conceal one gun due to how I was dressed. 4" N-Frame in a Matt Del Fatti Outside Waistband Holster with a Bruce Gibson Belt covered by a DHS Polo Shirt, one size too large, in navy blue, untucked. Never got made, and would've been confronted if the gun was "spotted".
Another part of it is moving in ways to minimize "telegraphing" your carry status. It's a long learning process, but I had some good teachers over the years and I hope some of you can use some of what I've said.
As far as Holsters and Belts, there are some good makers out there, but these are whom I use or have used and recommend:
Mitch Rosen
Milt Sparks
Matt Del Fatti
Bruce Gibson (Gibson ProRodeo, makes a great Belt)
Ted Blocker
Greg Kramer
The BeltMan
Don Hume (Pocket Holster)
Robert Mika (Pocket Holster)
Biker