First, yes, you do need a good belt. Though I have never even handled a belt from The Beltman, his belts do come highly recommended. I use an Aker B21, and an IWB very similar to the one pictured. The B21 is a kydex-reinforced belt that looks more like a dress belt than a gun belt. I ordinarily wear khakis or jeans and a sportcoat, so a big ol' Tactical Black belt that screams "GUNBELT!" wouldn't work for me. A sportcoat or jacket (depending on your climate and wardrobe, but not always feasible) goes a long way towards reducing printing.
I'm a lawyer, but I'm not your lawyer. If you need some honest-to-goodness legal advice, go buy some.