Dressing the "part"...benefits and drawbacks?

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Today I wore Carhart cargo shorts, a tee shirt, and trail running shoes. I had a flannel on early as it was a little cool. When I expect to be out in more brushy country I'll wear combat boots though.
 
I have pocket carried in all my everyday garb for some time. The only things I really changed when I started carrying a full size double stack IWB most of the time is that I started wearing more button down shirts, like Hawaiian shirts, fishing shirts, etc. I dont wear anything too tactical unless its a range day.
 
Five pages on style, starting with a question about something as abstract as the concept of a "tactical appearance", should suffice.
 
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