I have a Glock 19, Glock 29 and a S&W 642 that I'm about to alternate carrying all the time. I need to invest in some good leather but I can't decide if I want to do inside-the-pants or small-of-the-back. It has to be as completely concealed as possible while I'm carrying but also comfortable. Most of the time in the spring/summer I wear shorts and a polo untucked and in the fall/winter I wear jeans or khakis with a polo untucked with a jacket or a dress shirt tucked in but I can carry my 642 in an ankle holster in the winter if I'm tucked in. I want some insight before I blow $300+ in holsters and belts.

I'm in the same boat.  For me, it's down to a toss up between the Super Tuck and the Raven Concealment Phantom, with tuckable overhooks.  I would certainly also consider an M TAC, or a TT Gun Leather reinforced mout IWB, with tuckable hooks.  It's tough because there's nowhere to go try these out.  Good luck to you.

SOB has never done much for me. I'd recommend those holsters listed above or other IWB of your choice. Oh, PM sent.

No body likes Galco anymore?

I picked up a C-TAC for my Glock 19 and it's very comfortable.

There's so many choices out there, it's not even funny.

If you're truly talking about investing in leather, look at any number of custom makers - Sparks, Rosen, Alessi, Del Fatti, Andrews, Bulman, and many others.  You'll pay for it, and you'll wait for it, but the end result will be a work of art that'll last a lifetime.

If you want decent quality affordable leather without waiting 6 months or more, Galco, Don Hume, DeSantis, and Gould & Goodrich are some brands that stand out in my mind.

Kramer is a company I consider in between in terms of price and wait time.  I have to personal experience with them, but I understand they have a pretty quick turnaround, and their prices aren't too terribly bad.  I've been considering picking up a couple of Kramer belt scabbards sometime in the future.

On the gun boards, what gets recommended seems to run in waves, fads, whatever you want to call it.  Some of the standards are the VM II from Milt Sparks, Comp-Tac's C-tac, and the various hybrids such as the Minotaur, Crossbreed, etc.

In terms of decent, simple, relatively inexpensive OWB designs, Galco has the Combat Master, Gould & Goodrich has a model damnear identical to the Combat Master, Don Hume has the H721OT, and DeSantis has their Speed Scabbard.  Not as inexpensive, but not any better (IMO) is Galco's Concealable.  

You might also check out the offerings of Fist.  They're a custom maker, but I personally don't put them up there with Sparks, Alessi, etc.  Then again, you also won't be paying as much or waiting as long for the product, either.

Me?  I've been carrying my G19 in an Alessi CQC/S for the past few years.  I just recently got a Don Hume H721OT for it, as well.  I liked the design, and it was only $40.  Works just as good as any other OWB, but it probably wont last a lifetime like some of the high-dollar custom makers' stuff.  It's a good holster I don't mind scuffing up or otherwise abusing.

I carry the 642 in a Galco horsehide pocket holster, but only when I'm wearing some Carhartt shorts with pockets big enough for this method.

I carry my 3" GP100 and my S&W M&Ps in holsters I made myself.

Milt Sparks....check w/Lightning Arms Sports.

Quoted: SOB has never done much for me. I'd recommend those holsters listed above or other IWB of your choice. Oh, PM sent.

+1

i like CompTac (MTAC), TTGunleather/MiltSparks VM II, and threat solutions for IWB; pocket usually, but ankle sometimes

I got my Sparks SSII from brownells. Ordered it, got it 2 days later..
For my govt kimber eclipse.

Not a fan of small-of-the-back. (try sitting or worse falling backward) IWB arguably offers the most concealment.

www.miltsparks.com/

www.donhume.com/

www.safariland.com/concealment/  

Check out the Mister Softy IWB holster by High Noon Holsters.  It is very comfortable.  I could never get SOB to be comfortable.  I also worried about hurting my spine if I would fall on my back.

I ended up ordering a C-Tac, from Comp Tac.  Based on recommendations and my understanding of how they work, I believe the C-Tac will be the thinnest and most adjustable holster for me.  Being new to CCW, I think I may have to monkey with it some to get it how and where I'll be comfortable with it.  I'll let y'all know how it turns out, after I get it.

Galco Royal Guard, or the summer cheaper version, it has rough side in as opposed to the guard.  Carried my 640 in it today and forgot how I liked it as a change from pocket carry.

Comp-tac CTAC and Milt Sparks VM-II seems to be the best holsters out there right now.