I didn't want to sacrifice caliber, so I went with a 9mm Kahr CW9. I shoot it very well and it's fairly comfortable as far as compacts go. I decided to carry it religiously so in order to do that, I realized there's no magical holster that will work EVERY DAY for concealed carry.
Currently, I've got 6 different carry options for my Kahr CW9:
Maxpedition bag
PROS: You can carry a full size pistol, 4 mags and a box of ammo. Also throw in OC, flashlight, knife and kitchen sink. Plenty of room for tons of stuff and allows you to be free in your movement and is 100% concealable with latching/zipper pockets
CONS: Ok, as soon as I passed up my purse-phobia it was great. Only problem is you're trapped with carrying this bag around and can't exactly take it off and leave it anywhere. Makes draw very slow and carrying "bulky" with this bag bouncing off your hip.
Galco Sky-Ops IWB:
PROS: Extremely concealable. You can tuck your shirt into the holster or wear inder a T-shirt. The hold is low so the grip as slightly above your waistband and is fairly comfortable for all day carry
CONS: No shirt guard in an IWB is slightly uncomfortable sometimes.
Milt Sparks VMII:
PROS: This holster is the ultimate in comfort. Great IWB and holds the pistol perfectly. The shirt guard is a welcome sight and the design of the holster allos the holster to conform to your body making it cozy for all day wear.
CONS: Rides a little higher above the waistband than the Galco and a T-shirt is pupshing it a little for concealment. Might wanna grab a cover shirt for this one.
Galco Belly Band:
PROS: Great for carry no matter what you're wearing! Holds the pistol tight to your side and has a mag and wallet holder. Carry is left or right handed and the adjustable band is very comfortable. A great carry option for those who wear sweatpants or nothing at all.
CONS: Slight bit of roll when seated (might be my gut). The mag pouch is pretty short. Expect to be poked by your mag when seated.
Fanny Pack:
PROS: FAnny pack holster is easily worn and removed if needed. Makes the pistol accessible fairly quickly and can hold additional mags, wallet and others. Very comfortable all day wear
CONS: CAN be bulky depending on what you carry. Obviously a Kahr isn't going to bounce off your rear as much as a 1911 would. Accessing the main area for storage may cause you to "flash".
5.11 Vest:
PROS: Good concealment and easy to wear. Lightweight and lots of pockets for storage.
CONS: Putting in the 5.11 holster, the pistol would pull the vest down, causing it to sag. Not a great cary option in my opinion and in my opinion, a waste of money. Good thing I use it in IDPA..........
For the most part, I've been carrying IWB in the leather holsters. Fortunately, if I ever want to carry I don't have to worry about what I wear. I just change my method of carry. I've found it easier to change HOW I carry, rather than change WHAT I carry. Just makes more sense to me.
...............and that's my two cents.