One thing you might do is wear just the holster for a few days. If it is an IWB, just wear it and see if anyone notices the clips, straps or other fastenings. Plus you get a chance to get the feel before you have the full weight and bulk of your weapon.
If it passes with no trouble, then everything on a Friday or the last day of the week. Might be less likely to say anything. Then slowly start carrying every day of the week as your confidence in yourself and your equipment grows.