I second the comments about a good belt. You can get away with a lesser belt in IWB because the belt is outside the holster, applying pressure inward. (Not to say that a good belt doesn't help with IWB, too.) But with OWB, the holster is outside the belt, pulling down and away on the belt. A thin belt, or a belt without the right stuff, will quickly start to sag if carrying a pistol of any mass. Rather than holding the gun's grip high and tight, it will start to tilt outward, holding the gun less securely and making it more difficult to conceal.
For OWB, I'm a fan of leather gunbelts that have a Kydex insert, a la Comp-Tac or the Beltman. And the typical one-inch width of dress belts is right out. For me, 1.5" is the right width for OWB (I'd say 1.75" or 2", but it's hard to find even jeans with belt loops that large).
My OWB preference is a high-ride, leather, pancake-style holster. I don't carry all-leather IWB anymore, having switched about four years ago to the leather-Kydex hybrid MTAC. But the OWB pancake design in all-leather applies equal pressure to the sides of the holster resulting in a smooth, contoured profile and good tension on the gun for a snug, secure hold. There are a number of quality leatherworkers who make good pancake holsters like Tucker Gunleather, TT Gunleather, Kramer Handgun Leather, Ross Leather, and many more.
As to concealment garments, it shouldn't be much different than IWB unless you're lucky enough to be tall and on the slim side. Then, as previously mentioned, you may need to buy "tall" sizes, or go up one size above what you normally would wear. For those of us who are not
horizontally challenged

tall sizes are generally not necessary. But that's easy enough to determine without a holster. Just see where your shirts ride standing, sitting, bending, and doing your normal stuff. Depending upon the gun you choose to carry, the gun/holster combination probably won't reach below mid-hip.
Not including upper-body garment length, here is a short checklist I put together a few years ago:
- Thin fabric tends to print more; thick fabric tends to print less.
- One layer of a specific type of fabric tends to print more; two layers of the same fabric (e.g., two basic T-shirts instead of one) tend to print less.
- Rayon, nylon, some other synthetics, and silk blends cling as they drape and tend to print more; absorbent fibers like cotton and wool tend to print less (a caveat is that some rayon/polyester blends are woven thick, for winter wear, and don't print easily).
- Damp fabric tends to print more; dry fabric tends to print less (plan for what you normally do during Texas summers, and factor in perspiration if it's a factor).
- Simple, geometric patterns like straight lines tend to print more; complex patterns tend to print less.
- Light colors tend to print more; dark colors tend to print less (the contrast between light and shadow isn't as evident).
- Fitted clothing tends to print more; loose clothing tends to print less.
Body type and structure make a difference, too. If you have relatively wide shoulders compared to the width of your hips (and width of your "love handles" if they push the grip of the gun outward), you can easily carry just about anything at three o'clock. If you are thin and relatively straight up and down, three o'clock can still work, and you also might want to experiment with appendix carry somewhere between 12:30 and 1:30. If you have relatively wide hips (or aforementioned "successful lifestyle love handles"), you might find a sweet spot farther back at around 4:00 or 4:30. That's about as far to the rear as I would ever advise anyone to carry; I'm not a fan of small-of-back. I'd go with shoulder or even crossdraw before small-of-back.
Last up may be some experimentation with where you normally have the waist of your pants ride. I've seen some "successful lifestyle" body types cinch their belts essentially as hip-huggers, below the evidence of "Dunlap's Syndrome" (where some unwanted stuff has dun' lapped over your belt). A few conversations have led me to believe the core reason for that is vanity: with ample belly fat but not much around the hips, they can get away with claiming to wear a size 36 pair of jeans when it would be at least a size 42 if the pants were worn higher, at the real waistline.
For those guys, I'd seriously suggest some trials with bigger pants worn higher. A gun carried OWB would obviously ride higher if the pants were worn higher, but moreover there wouldn't be layers of extra cushioning pushing the grip of the gun away from the body. I've seen instances where the gun had to have been riding at a 20-degree angle to the plane of the body. Harder to conceal anything if it's sticking out sideways.
Conversely, that's why I love the gang-banger wannabe pants-on-the-ground look. Not only is it really hard to run or fight if your pants are halfway off, but it's almost impossible to belt-carry a firearm unless you keep one hand on your pants at all times to hold everything in place. One seriously wonders how that became a generation's "bad-boy" look when it's just about the least practical thing you can think of if you really wanted to be bad...
