I talk to gun owners everyday and the most common subject is carrying a gun concealed for self defense purposes. Normally, it doesn't matter if they have been shooting all of their life, or if they are thinking about their first handgun, they all have the same question. "What gun is the best for concealed carry?". I tell them the gun that feels the best to them and gives them the most comforting feeling that they are sufficiently armed is the way to go. If they buy a gun they can't manage to carry then its going to be at home when they are out and about and in need of their defensive weapon. Most of the customers determine that choosing the right gun will solve all of their problems. I explain to them that having the right gun is only half the solution.
I've found that while customers are willing to pay anywhere from $300 to $1200 for a good handgun, they don't want to spend more than $30 on a holster. Many don't intend to carry a gun in a holster at all. The ones that do are usually convinced that an Inside the Waist Band (IWB) holster is going to be to uncomfortable for daily carry. I haven't found one customer who has actually tried this method of carry before ruling it out.
I carry Browning Hi Powers and 1911's inside my waist band all day every day. I learned a long time ago that there are belts and holsters engineered for this specific purpose and they work very well. Most of my gear is made by Milt Sparks www.miltsparks.com. The belts they make are extra thick, not extra wide, to support the weight of full size firearm. I use their Versa Max II line of holsters shown above. They are very comfortable and once the leather forms to your particular body, they feel even more comfortable. The most popular holster series from the Milt Sparks line is the Summer Special. This is an old design and it's been copied by most other holster manufacturers. This holster is designed with the rough side of the leather on the outside of the holster to help it stay put when the weapon is drawn.
The Summer Special has been around for over 30 years and I don't see it losing popularity among those of us who carry handguns everyday. Like most of the Milt Sparks line, both the Versa Max II and the Summer Special need to be ordered with the proper sized belt loops. I use the smaller 1 1/4" loops because my dress pants won't take a 1 1/2" belt. However, if you wear denim jeans, cargo pants, or shorts most of the time, I recommend using the larger belt size and corresponding loops on your holster. Their is a noticeable difference in support from the wider belt.
Speaking of pants, carrying a gun concealed inside your waistband requires some forward thinking in this department as well. When I wear dress pants, I usually carry a small J-Frame revolver which is pretty light. When I wear jeans or heavier shorts, I'll carry a 1911 or Hi Power. For the larger guns, I buy my pants and belts 2 inches bigger in the waist. I've seen too many men with uncomfortable expressions on their faces from forcing a gun and holster in the back of their pants that were already on the tight side without the gun.
There are plenty of good holster manufacturers out there. I stick with Milt Sparks because I've never had a bad experience with their products or their customer service. However, Bianchi, Don Hume, Bulman Gun Leather, Alessi Gun Holsters, Galco, and DeSantis all make good products for concealed carry. Check out their products, give them a call, ask questions. I bought a few holsters, tried them for a month or so and then sold them on eBay before I found the ones I liked the best. It's a process. People spend hours, days, weeks and even months agonizing over which gun in what caliber will fit their CCW needs the best. Get a good, thick belt and start dedicating more time to your holster search and you too will come up with an IWB solution that is both comfortable, comforting, and concealable.