I've been carrying a glock 42 as my primary carry IWB. I switch between aiwb and 3-5. I've been wanting to try owb concealed, maybe with a glock 19 or something. I generally wear t-shirts all year, and a jacket or fleece when needed. What's a good owb holster that conceals fairly well? I like kydex or maybe leather. And maybe something higher riding to conceal better?

I use a Winthrop leather OWB for my Shield. it hides well, I think because the rake is more than usual.
it  looks like maybe 25 degrees or so.
For my G19, believe it or not, the Glock Sport Holster works very well, it holds close and tight. Maybe try it
first, and if you dont like it, big deal, its like $14 on Amazon.
The Winthrop is on Amazon too.

Before I went solely to IWB I used to carry a Colt Commander OWB in a Milt Sparks 55BN.



It holds the pistol firmly into your body and is easy to conceal with a loose shirt or T shirt.

I'm wearing a Bianchi Remedy with my full size M&P 9.  Just got it for Christmas, so far so good.  Kydek reinforced leather.

I really like cook's holsters so I was thinking of trying this. Thoughts?

http://www.cooksholsters.com/comfort-series-owb-iwb-holster/

Alessi CQC/S

DeSantis for my Keltec P11, Clament's Custom Leather for my SR9c & SR45.

I have a good pancake holster by Don Hume.  It does a fantastic job of holding my S&W 1076 in tight at my side.  

Pretty much any of the big names' pancake style works great.  I have some for open carry (thumb break) and some for concealed carry of my 1911s or the 1076.  I really need to find one for the little XDs too.

I also like cross-draw carry as well.

I carry a G19 in a Raven Phantom OWB under an untucked t-shirt or Polo.

Yep. Throw on some pancake wings and it really disappears.

I'm a big fan of the X Comcealment "C" holster for OWB.

Raven Concealment.

This

Ive got several IWB and OWB holsters from Black Point Tactical and they do the trick. Give them the ole Google-roo.

Leather is more comfortable to me. I've had a few Kydex (Raven, Bravo, OTG, etc) and keep coming back to my Tucker and Byrd pancake.

That looks like my next Holster

Dark Star Gear.

I'll throw Liion out there.   Don't have one but they looked interesting.

This, but with a Glock 22

Glock Sport Combat holster FTMFW

I have a DeSantis and just started with a Blackhawk. I carry a G19 every day.

Raven makes a good holster but it is worn best at the 4:00 position where it sits flattest against the body. I tried it at 3:00 and it just stuck out too much. JM Custom kydex hugs the body more closely than the Raven, but you are looking at a 8-9 week wait for one versus a week for a quick-ship Raven.

 

I don't care for 4:00 either or anything behind the hip for that matter. It prints terribly on me and my shirt always hangs up, but the weather is colder so I can throw on a jacket to aid in concealment. 4:00 doesn't bulge as much as 3:00 on me, though. Appendix position is my preferred. I just don't have a holster for IWB at this time.

 

+1 Lots of fans out there of appendix carry. I've tried it so many times and just completely hate it.

I am 5'10" with a 29" inseam (I think it's more like 28"!).  I don't think I could possibly comfortably sit down with something rigid stuck down there hitting me in the leg or somewhere worse.

The COOKS is pretty good--I have the "wings" on mine; it's held much closer against my body than the blackpoint tactical with leather wings (but I'm upside down pear shaped).  The Raven's aren't bad, but aren't quite as good as the Cooks.  My second favorite OWB is a Gideon Elite holster by Dale Fricke--I use it the most in classes (but I think x-concealment's GEN2 "C" SERIES COMPACT OWB is cheaper and will hold close to the body).

Because of my big belly and lack of any waist or butt, I didn't think IWB was possible--but so far, the RM Holsters "low rider" has been great--though I do wish it held the gun up another 1/2"-1" higher (but who knows if I'd love it as much).  It's nice not worrying about the bottom of the holster not being visible.
It's all I use now, so I sold the blackpoint and may sell the raven (but it's the only holster I have that fits a TLR, so I doubt it), and the cooks (though it was my favorite of the 4 or 5 OWBs I tried).  Note:  I DO think the Cooks OWB comfort carry worked even a bit better with the SHIELD than the G19--I even kept my old one in case I get another SHIELD down the road.

In the end, I think you just have to buy like 4-6 and figure out what works best for you.
I'm about to buy 2-3 more IWBs to try out based on people's recommendations now that I know it IS possible.