A question to the rather larger people who everyday care.
Do you order one size larger shirts because of caring OWB?
And do you order regular length or tall man ?
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One size larger or relaxed fit. Almost always tall or Duluth trading post long tail (?) shirts.
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Being a person who carries a certain number of '“x’s”, I share your experience.
Here are my guidelines:
- I shouldn’t be able to feel my shirt pulling against my weapon.
- I carry IWB, but I still want my shirt to come down as low as the bottom of the holster.
- The shirt should be loose enough to be lifted easily to access the grip and draw.
I make my own shirts, so I just add a little extra room on my carry side. Be careful when buying shirts off the rack since the actual size/length of a 3xl can vary widely from one manufacturer to another. I can comfortably wear anything from a 1x to a 3x depending on who made it. Best thing is to try it on before buying, to make sure it fits where you need it to fit.
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Typically i wear a shirt tucked in and go slightly larger on an over shirt or light coat.
As a larger person, it’s usually easier and less expensive to go up a size rather than find a “tall” size.
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Yes to one size larger and tall!
I really look forward to the cooler months when a vest or jacket is not out of place!
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I have been leaning more towards “relaxed fit” myself. Nancy calls them “buffet pants”. 
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Shop big & tall menswear. Carhartt is also good.
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I have always worn clothing that is larger since I do not like clothing to be restrictive, it’s very uncomfortable for me.
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42" waist is my size but 44" feel so comfortable I buy 46"!
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