I do pretty much everyday. I use two different leather, pancake type holsters.
I carry crossdraw and the guns in recent years that I've carried can be a little hard to find a holster for. Especially crossdraw holsters that aren't made by some small shop for $200+. Now before I switched back to a Beretta 92 variant a few months ago. I carried a CZ-75 Phantom for 3 years or so. I love that gun. But again, finding a holster I wanted to be able to use OWB (leather and for crossdraw) is challenging. I could never find one made specifically for the the Phantom. So I compared the Phantom's dimensions. It's pretty close to the full sized Glock 20 and the full sized .45 Glocks. The holster worked easily for the Phantom. And when I switched to my current EDC, my Beretta Brig Tac. I was happy to see the Brig Tac with rail and brigadier slide fit just fine. I use a Bianchi 7 Shadow 2 holster: http://www.midwayusa.com/product/504585/bianchi-7-shadow-2-holster-glock-20-21-s-and-w-m-and-p-leather?cm_mmc=S_Spop-Email-_-Service_Emails-_-ShippingConf-_-ProductLink It can be used either strongside, or crossdraw. And it hugs the body pretty well.
I also wanted to be able to carry my Brig Tac with a light sometimes. Once again, crossdraw, brig slide, light and leather. Not an easy find. I settled and hoped that a Desantis Tac-Lite holster for a Glock l7 would work. Believe me, it was a very tight fit and still is a little tight. Getting the thumb break over the end of the gun was a chore. But I've been breaking it in the last couple weeks and it will work just fine. http://www.desantisholster.com/THE-TAC-LITE Holster is a little small for the gun and light combo. But given a little more time. It will be pretty close to perfect for me.
As long as you don't get too crazy. You can probably find a holster for exactly like a M9/92 or M&P. That Bianchi above is made specifically for the Glock and MP.
As for cover garments. Sometimes I open carry. Where I live it's not big deal at all. I don't OC all the time. If I took small family members to a Chuck-E-Cheese type place. With a bunch of kids running around. And a bunch of lemming type parents. I'd definitely conceal as to not make a scene. But anyway, for concealing it depends on what I'm wearing. If it's not really cold out and I just wearing normal clothes. Jeans and similar. A simple thing like a baseball jersey works fine. Or if it's cold, but not freezing. A simple vest (not some obvious photographer/tactical vest) like a fleece or water resistant type vest works great. As does a normal jacket of any kind. A simple buttoned/unbuttoned over shirt works great too. If you're wanting a more dressier look. But you're not wearing a suit. A dress suit jacket, sport coat, etc and some jeans work great. Think Raylan Givens from Justified.
The trick is to make sure the holster holds the gun to your body pretty close and that your cover garment isn't too small and tight. I have a friend. Super nice guy and smart too. But he carried a Glock l7 or similar in a Blackhawk Serpa holster. Wore a jacket or whatever to cover it. Maybe it wasn't super obvious to everyone what he had on his hip. But it looked very obvious that something was there.