Check out this post by Tim at Gunnuts Media, then come back. I started to leave this as a comment, and realized I was hijacking the post, so I will comment here.
I had a great moment last night in a grocery in Oregon. I open carry as a matter of course, and have drawn far more complements on it than otherwise. Only once have I been asked to refrain, and then it was very polite, and I have honored that request (mostly by not going there, but there you have it).
That being said, I have in recent years started taking much more care in the image I present. I've gone from torn jeans and sleeveless tshirts to wearing casual, clean buttondown shirts. I never wear my torn or stained clothing in public while armed. I traded out my well-loved canvas jacket for a classy leather one. My goal, going armed in public, is to present myself as stable, polite, and responsible.
These days, I am a new father, so that adds another layer in things- literally. I am usually the one that is carrying little Danger around the store. I figure My Lovely Wife packed him around for quite some time already, so its my turn. Which means I am out in public, armed, with a very small child in one if those Swedish Marsupial kid carriers. Trust me, its quite a look.
But its hard to argue with image. The people we are trying to reach are not those on our fringe, or even on our side. Its the ones in the middle, that haven't made their minds up. But maybe, yesterday in a grocery store in Oregon, people saw a young father, nicely dressed, carrying his son and a pistol and thought, 'Maybe that's what a gun owner looks like.' And maybe they changed their minds about gun control. I couldn't do that if I was still wearing torn up old jeans and a sleeveless tee with my tattoos showing.