I have 1 of every shirt offered by the NRA on the online store, my son (16 years old) has a few too, my wife has several as well.
Do I wear them ALL THE TIME??? No
But I do wear them often, and I wear them proudly...It is not meant to advertise that I am carrying a gun (even though I am carrying one...or 2)...It is meant to advertise my political point of view, and to say that I'M NOT ASHAMED OF IT.
I wear mine to work, out around town, pretty much anywhere...my son wears one of his to school, its the one that says "The right of the People to keep and bear arms shall not be infringed" because that one has no guns pictured, if it had pics of guns on it they would not let him wear it...they don't like it, but they can't really stop it and besides, I don't really care what they do or don't like. They won't be "influencing" my son with their twisted views...and they know it.
I went to the last parent teachers conference wearing the one that says "Family, Freedom & Firearms...Welcome To My World" (several guns pictured on it too)...my sons ROTC teacher (a marine) just smiled and said "Give em hell"...
I'm not an anarchist or anything of the sort...but I'm Free to speak my mind ANYWHERE. I'm well versed, well educated, well dressed (IMO), and I'm all too eager to debate the subject of Freedom and/or firearms with anybody...anybody.