This is basically what I did.
I started by wearing my gun, CZ83 in a Yaqui style owb holster, in my holster at all times possible while in the house and secure in knowing I wasn't going to boo-boo in any way because there was no way I could. Who could see me? After I got comfortable with that after a few days, a short jaunt to the local WallyWorld to pick up some milk and bread. I was of course, overdressed with my leather jacket on a semi mild and fairly warm day. The next day was warmer so I set out in a thick t-shirt and jeans to the local tradin' post. The only person that noticed anything different that day was the guy I was talking to about buying a new rifle at the tradin' post, and he only gave me a small knowing look that said I was doing okay with it.
Now don't get me wrong, I'm not trying to show anything, or even attempt to hide anything, I think, as was mentioned before, you just have to "forget" it's there and go on with a normal routine. Just remember the purpose. I hate to say this but, most people don't/won't notice anything unless it's grossly out of place.
Oh yeah, the first time I walked out of the house with my gun on, I felt as though I had a spotlight shining on me and a neon sign flashing on all sides of me