Jimmy Dean:
Some really good advice has been posted, if you can weed out the silly "I do this, so you should too" stuff.
1911 covered most of it:
* Get a good belt. Wilderness if you like nylon, the Beltman if you want leather. Ignore the folks that tell you it doesn't matter. wearing lightweight clothing (I live in Baton Rouge) makes the belt important. it will let the holster hug your body tighter.
* Get a good holster. if you want an IWB holster, by all means get one. I carry all day, every day in an OWB. With a good belt and a good holster you can do this. FWIW My EDC is a Glock 19. I can wear a dark T-shirt or a dark/patterned 'camp" shirt (squared off shirttail, untucked) w/ OWB holster any time. Comp-Tac (
www.comp-tac.com) is a good place to start looking.
Before you start looking at all the shoulder, Thunderwear, SOB stuff, make an honest assessment of how you'd access your gun in a struggle. Most folks, including most instructors, use strong side carry.
* DO NOT compromise on your weapon just to make it easy to conceal. As Clint Smith will tell you, if your gun is really comfortable to carry, you are probably carrying the wrong gun. Please don't stoop to the Kel-Tecs. I have one. It's a backup for my BUG. To me, that's about all they are good for. Make sure you are carrying a
dependable handgun.
* Buy your shirts (dark and/or patterned) a little on the large size. Academy and Wal-Mart have plenty to choose from. Believe me, you can carry OWB with just a T-shirt. BUT, you have to dress around the gun in the hot weather we get down here. For four or five months of the year you can wear a coat, windbreaker, vest , etc. After April, get a good belt, get a good holster, and dress around the gun.
Clint will also tell you that carrying a handgun isn't supposed to comfortable...it's supposed to comforting.
For those offended by the Kel-Tec comment......at least I didn't tell Jimmy how crummy the Fobus holsters are.