It's been 16 years that I've been carrying a handgun concealed on my person on a daily basis. This seems like a good time to review and evaluate my past and present concealed carry choices. Let's start at the beginning.
I purchased my first handgun, a H&K USP, full-size, in .45 ACP in 2001. That purchase was driven by a couple factors:
It was "the bad old days" before the sunset of the Assault Weapons Ban, so normal capacity magazines for handguns were very expensive, where they were allowed. I lived in California, so none for me. I had heard a lot of misinformation about the relative efficacy of 9mm, .40 S&W, and .45 ACP. I really only considered .40 S&W and .45 ACP.
I wanted a full-size gun, since they're easier to shoot, and I didn't view concealed carry as a possibility, because it wasn't legal where I lived and worked.
The technological wizardry of the USP (what part of Universal Self-loading Pistol don't you understand?) kinda dazzled me. I considered purchasing a Glock 21. I really liked the fact that I didn't have to decide on an operating mode up front, and the single action trigger was pretty nice.
(Honestly, if a little embarrassingly) I had read about the USP in the novel Rainbow Six, and the Internet confirmed that It Was Good. Further cementing its awesomeness, when I showed up to my California Handgun Safety class, all of the instructors were carrying full-sized USPs in .40 S&W.
When I moved to a concealed-carry-friendly neighborhood (Seattle, WA) I immediately applied for a CPL (Concealed Pistol License). Upon its receipt a few weeks later, I zipped down to my local gun shop, Weapons Safety, Inc. in Bellevue, WA (RIP) and purchased a Nylon IWB/OWB holster with a thumb break and integrated magazine pouch for $20. I can't clearly recall, but because I hadn't learned how to draw (and certainly not from concealment) I wouldn't bet money that I ever even practiced a single draw from that thing. It was very uncomfortable because USPs are heavy and huge, the holster tilted and shifted around constantly. I was using a department-store one-inch-wide leather dress belt. I couldn't have re-holstered the gun because the holster collapsed and flattened as soon as the gun was removed.
I wore it for about three weeks, before my new co-workers saved me from myself. I had a hard time finding a job when I moved to Seattle, but eventually got a job as a gun salesman and range safety officer at the gun shop I bought the holster from. The very first thing they did was throw my holster in the trash, find me a new one, a magazine carrier, and suggest that I buy a $100 Galco belt. They handed me a leather Galco paddle holster. I can't recall exactly which model it was, but I do remember that it was actually for a USP compact instead of a USP full-size, which means that the muzzle (and more importantly the front sight) hung down below the open bottom of the holster. This was far from perfect, but a major improvement. Had I purchased a more common gun I would have been more likely to find a better holster. I bought a better, wider, stiffer belt from Fred Meyer, but it took years before I heeded the advice to purchase a purpose-built gun belt.
The weather in Seattle is cool and I was a pretty slender guy (acclimated to south central Texas), so my constant need of a fleece vest, jacket, or coat made it pretty easy to conceal even such a large gun, and I carried it for more than a year before I considered anything different. Working in a gun shop and range, where open carry was permissible made innovation and improvement a fairly low priority. My friends there were all "gun guys" and even printing a little was no big deal. However, there were times I just couldn't carry because the USP was too big.
One day a used Smith & Wesson 442 came through the shop for a good price, and I purchased it immediately. It would remain my deep concealment carry gun until 2017. I carried it in an ankle holster while dressed up or an IWB holster while dressed down. It was easy to conceal it in anything from a suit and tie, to business casual, to shorts and a t-shirt.
But it wasn't all great news. While standing, ankle holsters are incredibly slow to draw from, and impossible to do so subtly. They're difficult to access in a tussle. Small, light revolvers have crummy sights, triggers, recoil much more sharply than a larger handgun, hold little ammo, and range from average to glacially slow to reload depending on user skill and the method of carrying extra ammo (e.g., a speed-loader vs. speed strips vs. moon clips).
Middle Ground, Take 1
Near the end of my time at the gun shop, I had the opportunity to purchase a Kahr P9 at a great price and jumped on it. Along with Blade-Tech's original IWB holster (which they don't appear to make anymore) and single mag carrier, I had a very concealable, very comfortable rig I could carry in most clothing. The stock sights were metal and pretty decent in terms of marking (no misaligned three dots). Although I still carried the J-frame in formal-wear, I carried this setup daily for the next six years. In hindsight, I think this was a pretty natural reaction to carrying the USP for a couple years; that thing was a boat anchor. This was the first concealed carry rig I owned that I wouldn't be ashamed to suggest to a student today. In case you missed it, I'll reiterate: I worked in a gun shop and it took me almost two years to get a concealed carry rig that didn't suck.
When I later started to take classes that pushed my accuracy and speed, I found that the Kahr didn't actually fit my hands very well. While the length of pull (distance from the backstrap to trigger face) measured while the trigger was at rest was comfortable, the point at which the trigger actually broke each shot forced me to curl my index finger up quite a bit past a 90 degree angle of the proximal (middle) joint of my finger. The Kahr holds more ammo and reloads much faster than a 5-shot revolver, but is a 7+1 gun.
Middle Ground, Take 2
After starting to take more challenging training classes in 2009, I had to admit that although the Kahr P9 was a pleasure to carry, I wasn't shooting great with it. So I migrated in 2011 to a Glock 23 with Dawson Precision sights (Charger rear and slightly narrower fiber optic front) in a Comp-Tac C-Tac holster (thanks to advice from Karl Rehn) and a number of different magazine carriers.
About this time -- which is to say many years later than necessary -- I discovered the joy of purpose-built gun belts. For eight years I carried on the thickest, widest, stiffest, department store leather belt I could find on the rack. That is to say I carried on a thin, narrow, floppy leather fashion belt with a flimsy buckle. As soon as I put on my Wilderness Instructor Belt, I knew what I'd been missing. I've worn that belt almost daily since about 2009 and it's still in pretty good shape. It's only two or three times what you'd pay for a belt at a department store, but it's worth much more in terms of comfort, improved conceal-ability, sturdiness, and longevity. I'm positive I had to throw away at least three department store belts in the same amount of time that had broken or worn out. You can certainly make it work, but if you can afford the $60 for a purpose-made belt, it's just about the best money you can spend to improve your concealed carry experience.
I stuck with the Glock 23 for a couple years. When I took the Rangemaster Instructor Development Course, I recognized that .40 S&W recoil was limiting the speed of my follow-up shots and beating up my hands. I opted to stick with the platform and gear and just move to 9mm (the Glock 19).
I worked at the indoor range in Seattle where InSights Training was based in the early 2000s. Their standard advice to shooters goes something like this, "Stop reading gun reviews, buy a Glock 19, a Kramer #2 IWB holster and belt, get good training, and shoot a lot. By the time you've shot enough to have an opinion, you'll probably agree with us."
That's good advice.