Did you get it right - the very first time?

I'm kinda with Colbad on this issue. I've done much filtering during my three or so years of ccw. I float among the following, dependent upon clothing/comfort/need, in order of most-routinely-carried:

Sig P938 with Stoner IWB or Crossbreed single clip mini-tuck (cut front clip off to mimic micro clip for p238)

Glock 27 with Stoner IWB

Ruger LCP or Sig P238 if I have to go that low in caliber/size.

Two most recent additions getting some play due to size/caliber ratio:

XDS .45 in Don Hume soft pocket single clip IWB

Kahr CM40 - owned for just two weeks now, no holster yet as I wait to see if reliable. Love size and caliber but reliability I'm not 100% on yet. Fired 100 rds with 9 intermittent FTF's. Optimistic though. Break in period is 200+ rds. It will get benched if feed issues continue. So, that one might be in the "didn't get right" pile eventually or my favorite, who knows??

SW 442CT airweight in ccw arsenal but never bought ccw holster, thinking about it though to throw into mix.

I've tried many holsters. Lots of cheap, horrible ones out there. Top filtered choices are Stoner leather IWB w/body shield - deep conceal option, Don Hume soft pocket - same seating depth as stoner, and Crossbreed with one clip - either mini-tuck or micro clip. It just takes me too long to put on a double clip! Best ankle one is the Galco Ankle Lite, IMO, but rarely use.

The search for perfect CCW gun continues...Holster figured out though - Stoner IWB for whichever one is my majority carry gun!
 
I don't think it's possible to get it right on the first try unless you get very lucky or have a generous friend who lets you try lots of their stuff before you buy. You have to actually try carrying to figure out what you want and need.

I started out with a G19 and a N82 IWB holster. Very comfortable and good retention but I couldn't ever manage to figure out how to get the holster to stay in place and particularly at the angle I wanted since it only had one clip.

Then I went to a Crossbreed Supertuck. Not quite as comfortable and basically no retention but at least everything would stay in place.

Now I'm on a "Phoenix" by Nelson Holsters (local guy) which is very comfortable, has good retention and will stay in place. I think I'll be sticking with it for a while.

I also added a G26 to the mix because sometimes I want to carry less than the G19 but more than my LCP.
 
First handgun I bought after turning 21 was an SW9VE. 4 years later, still carrying it. At first I carried in an uncle mike's IWB at 3:00 and an OWB uncle mike's at 3:00. Now I go back and forth between a forward canted OWB holster from galco, and a Blackhawk serpa level II CQC holster in paddle formation, and a Blackhawk beltslide holster I use mainly as in IWB holster.

The only thing I have really changed is using different holsters for different situations. Galco with a forward cant positioned at 5:30 while I am wearing a suit, Blackhawk beltslide IWB at 3:00 when carrying concealed in casual clothing, Blackhawk CQC level II when carrying in the open or under a sweatshirt or jacket, also at 3:00.
 
Went from a Sig SP2022 (first pistol, didn't realize there were hardly any holsters at the time) to a P239; then to a Glock 19/26 which is what I still carry. Mostly the 19 now, AIWB in a VG2.
 
I got my carry permit a couple of years ago. Having grown up in disarmed communities (NYC and then Massachusetts for college), I found it weird at first. So I began a conditioning process. IWB and OWB just never were comfortable for me, so I started pocket holster carrying a Colt Jr. in .25.

Don't get me wrong, I don't really feel undergunned with it because it has minute of 9-ring B27 accuracy at 9 yards. But the nice thing was that it didn't print, didn't clink in the holster, and allowed me to cock the hammer with the safety on to prevent a negligent discharge if I slipped.

My first pocket holster was a DeSantis Nemesis. Then I saw a pocket holster with a flat back at a local gun show (this one made by a local craftsman) and never went back. It looks like a wallet on one side, but the other has the holster-pistol combination in it. Anyway, I started in winter, so I was coat pocket carrying. The nice thing about the wallet-style backing is that one really can discretely transfer between pants pocket and coat pocket.

Once I got used to having a pistol in my pocket (took about 3 months), I went up a notch in caliber and started carrying a Beretta Tomcat or NAA Guardian .32 in a similar pocket holster. Now I carry a Colt Pony .380 with a Remora pocket holster in winter, and the Tomcat or Colt Jr. in pants in summer.
 
First gun I bought for CCW was an M&P9C and I'm still carrying it today. I initially bought a desantis mini slide to carry it in and that was a total failure. The holster was molded on the belt side, and worked fine with a cheap belt but the mouth closed in when I used a heavier gun belt.
I liked the size, and angle of the desantis so I used it as a pattern and made my own out of much heavier leather, and kept the belt side of the holster flat. I've been using this rig for several years now.

Since then I've experimented with making IWB holters and have come up with several variations I use from time to time, but for the most part I prefer carrying OWB with the slide holster. I have also added an LCP for warm weather carry as the M&P is hard to conceal with a T-shirt.
 
My experience was different then what I wanted. I lived in Massachusetts and got my first permit here, and the gun that I wanted was the Kahr K40 and it was banned. Finding a preban one was pretty difficult, so the first gun I bought was a S&W M&P Compact in .40 with a sucky Uncle Mike's holster. This is particularly interesting to me in retrospect because I carry a Kahr K9 to this day, which I consider ideal. So I guess circumstances forced me away from the right gun albeit the wrong caliber, but I would never have made the correct holster choice, which I currently use a TT Gunleather Mike's Special to carry it in (which also is strangely similar in name to my first holster. Huh.)
 
Just about everything about my views has changed.

My wife wanted something she could shoot for home protection and we bought a Ruger 22/45 Lite pistol as advised by my son, who shoots a CZ 9mm.

I decided to get a small caliber rifle and (again under advice) I got a Ruger 10/22. Lots of fun, but when the shortage occurred, I decided to try Savage 17hmr, which seemed a little easier to find ammo. I now prefer the bolt action rifle. I take my time aiming each shot, and bolt action just seems to be part of settling down to hold steady ad take aim.

After a few years of shooting, I like what I have, but I want a pistol with a little more power. Also 22lr is still not in good supply and my 22/45 is a little picky and won't cycle properly on many brands. I like my son's CZ, but it is designed for a different style of shooting, so I am going to add a large frame 9mm.
 
I wouldn't say I have a perfect option yet, but I've been through I believe ten carry guns and probably triple that number of holsters. The holsters are much worse than the guns... you never know if the darn thing is actually going to be comfortable for you or not.
 
I blew it big time. The first gun I've ever owned or shot was the worst possible choice. A Taurus .357 magnum 7 shot snub nose. I picked the worst possible everything. Oh yeah, and it was not before a few range trips that I found out I could use .38 specials. Needless to say I developed quite a flinch.
 
My first handgun purchase was a S&W Bodyguard .380 and it's still my edc. I carry it with a THEIS IWB holster and am still very happy with the setup.
 
I first purchased a S&W SD40VE for carry, when I had my CCDW class scheduled.

I never did carry that one. I just hated the thing and ended up trading up to a Kimber Tac Pro 2. I carry that in cooler weather in a kydex IWB holster, or occassionally OWB.

I use a Ruger SP101 .357 for summer time in a cheapy nylon IWB clip type holster. It rides very low that way, with just the grip peaking out so it is fine in the summer with light clothing.

The best carry accessory I got was a nice stiff gun belt that has a kydex liner to hold its shape. That keeps my Kimber riding in one place.

I'm still not exactly happy, though.
 
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