Thought I'd revisit this post- as I recently have been evaluating different holster types myself.
For IWB: I've carried Galco King Tux. Pretty equivalent to Crossbreed Supertuck. Those are both commonly dubbed as the most comfortable mainstream IWB. Many instructors will recommend them. The only gripe I have about when I have to buy pants that are 2" bigger in the waist to accommodate a Glock G26/G19
For OWB: bought a custom hard-shell holster molded to fit my Glock G26. Now- that's a lot more comfortable in the waist because it's not consuming your pants, and slightly faster draw, but it's more conspicuous than IWB. Although this is a forum for open carry so I guess conspicuous is a moot point here. I wish I could remember the company that made it. I bought it at a gun show a year ago.
Wallet / pocket holsters: if you're looking for concealed and very comfortable, and stylish, check out this site:
www.pockholsters.com With these holsters you're limited to a sub-compact firearm that fits in your pocket, but from the YouTube videos and reviews I read of these the holsters are (most importantly) safe, and appear pretty comfortable. I ordered one for myself and plan on carrying it when I prefer to conceal instead of my usual OC. Gives you the benefit of the conceal-ability without sacrificing the waistline of your pants. If I like this holster I plan on having my front pockets tailored to be a bit deeper on my jeans and expand the pockets on a few of my suit coats.
Belly bands: this type I don't have. Again, a bit out of the scope of this forum because belly band holsters are for deep concealment. However one of my coworkers has a belly band style holster and loves it. It offers more comfort than the IWB, can be worn in multiple positions- above the waist line around the belly, or below the waistline. And it usually has pouches for extra magazines which is always a good thing. Only negative is a potentially very slow draw.
After listening to a lot of holster advise I'm come to conclude its a very personal decision. A single gun/holster combination for one person may be excellent, while not preferred by another. If you have some friends in the 2A community with holsters made for your firearm, I'd you could borrow and carry a few different ones, that's what I'd recommend. Saves your $$ on buying a few different ones until you settle on one you most prefer.
That's my .02 or rather $2
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