I think a big part of this is your mentality on things too, and that goes in a couple of directions. Most of the people I know that carry do so on an irregular basis. Carrying "when you feel or perceive the need" seems to be the general thought or maybe special occasions, etc.
I don't think most look at it as part of their lifestyle, which to me, if you're going to carry a gun, that's how you should be looking at it. Unless you're lucky enough to have one of those gun specific Magic 8 Balls to tell you what you're going to need and when youll need it, there is only one way to cover things, and that's to always have a gun on you, and preferably, one that will cover the gamut of things a handgun might have to.
Once you figure out what you shoot best with, what gear works best with it, and where on your body to carry it, then it just fades into the obscurity of everything else you carry around on you every day and you dont even know its there 99% of the time.
The other thing mentality wise has to do with concealing the gun. Your general attitude and bearing, makes a big difference in things. Gun or not, if you go about your day as if you belong there, wherever that is and act like it, grab and hold eye contact, acknowledge or engage people who "might" pay attention to you, etc, ignore the fact you have a gun on you, no matter what you're wearing, and act like anyone else who isn't carrying one, you'll have a different experience than someone who is obviously self-conscious, acting "quirky" and "off", and constantly checking themselves, be that with their hands or eyes, ect. Act like you're "up to something", or just a little "off", and even those who are self-absorbed and/or with their heads buried in their phones, will pick up on that pretty quick, if they bother to look at you.