I refuse to dress around my gun. I am fortunate enough to live in an open carry state (Washington). I have a paddle holster so I have don't have to make any allowances in my clothing. The only allowance I make is that I always wear a t-shirt tucked in because I don't like the feel of the bare butt of the gun against my skin if I should choose to flip my outer shirt over it to conceal it.
My feeling is that if I am wearing a shirt that is tucked in and covers the gun, then I probably wouldn't be able to deploy the gun quick enough anyway. So, if I desire to conceal the gun, just any regular untucked shirt flipped over the gun is all there is, or if it is cool enough to wear a jacket the jacket covers the gun, if I choose.
It's a lot easier to just wear an OWB holster and not have to mess with special fitting clothing.