Man this thread has covered a big range from holster advise to fashion.
OP: Since you know leather and belts here's my take assuming you have that part covered.
IME, your body shape has a major part of how a gun fits/carries. I've seen more folks who are skinny have issues with concealment vs. those who carry more weight.
IMO, concealment is not only out of sight but unrecognized. With that generally carrying at 3-9 o'clock will print the most. As the body is shaped, those two points are the end points of your body; Adding to it will generally make you look wider than normal even with loose fitting clothing.
For that reason most carry forward or behind those points.
Every spot has its pros and cons and depending on your body shape some may not be an option.
Generally the length of a gun doesn't affect the difficulty of carrying concealed as the width (within reason). I find carrying a 5" 1911 is easier than an M&P FS, Sig 229, G22, or other double stack pistol. Easier being more comfortable and more concealable.
The grip on some guns will also make a big difference on 'printing'. Generally mag wells, magazine extensions and the like enhance the problem.
Aside from a P232 380, I have always preferred to carry a full size gun. The 232 satisfied my desire to always carry vs. being required to carry the only other authorized weapon P229. It was easy to put the 232 pretty much anywhere for a quick trip out.
Our off-duty carry policy has changed now to allow a greater range of guns, so I'm back to FS guns.
YMMV.