I've carried concealed many places usually just doing normal errands, I've gotten haircuts before and not worried about it, I generally just wear jeans, an undershirt and a button up shirt untucked over it... seems to hide things nicely... no one has ever noticed me.
On another note I also carry a cell phone so most people are used to seeing me with a 'buldge' at my side, generally when carrying I move the phone to my pocket since my strong side is also my strong cell side
Most people don't see me as the gun type and many would call me 'approachable' and complete strangers have a habit of talking to me, I don't mind it but if they touched me that would be different.
My family doesn't hug much so I don't have to worry about it there, and occassionally I dress up, but I've never dressed and carried at the same time... I too get the CIA/FBI comments, if they only knew! haha
I think as carriers we all feel sometimes we've been 'made', but you have to realize in reality people are really obvlivious to what's going on. I've seen it everyday people swerving across lanes of traffic not paying attention. People running into me in the stores with carts and stuff. It's not nice but at the same time if these people can't pay what little attention they need for motor skills how can they 'make' or even realize that the buldge or object at your side is a gun.
I think with the increase use of cellular phones people expect it to be a phone and most won't admit that it could be a gun. Or maybe a cellular gun, who knows... ( I saw one someplace a little .22 zip gun) Ya never know and because we carry we have the stereotype or the 'ability' to see the other aspects of what someone might have under their shirt or coat. We as practicioners of our 2nd ammendment rights are not nearly as nieve... we cannot afford to be, we HAVE to pay attention.