I'm in the camp of having come full circle. Started carrying in the mid 80s, Army MP 1911. Then we crossed over to the 92FS. When I left the Army I continued to carry the 92FS as a LEO (not an LEO now). When I left polo e work I rediscovered the 1911 (note: I have had and always will own a 92FS) and started training and carrying it, full size Colt 70 series.
Then I became a member of the "Oh it's the new gun of the month" club. Tried glocks when they were called the weird plastic guns, like the Turkish Ghost. Tried most make of revolver, they never floated my skirt up save for the colt lawman series.
Holsters. I've always spent the money for a good holster and belt. I was taught that early on. I have, or try to, 3 holsters for my current carry gun, OWB, Paddle, and IWB. Just to have options. I also have a shoulder holster that I use when traveling.
Now after trying most of the popular guns of the last 25 years, the ones I carry most are 1911s or Beretta 92. I am well practiced and comfortable with either. I agree with the keep it simple principle, and carry guns with similar actions and similar in function. Example, Sigs are similar to Berettas and HKs are similar to 1911s.
My carry set up is straight forward. Firearm in a good holster, at least 2 spare mags. Period. It's like wearing a watch. As soon as I get dressed in the morning, the gun is just like another article of clothing. No big deal.
I will echo what others have said about practice. If you are serious about carrying a weapon, about protecting your life and your families, practice
is a must. Practice with the gun you carry, with the Ammo you carry if at all possible.
If you want to dress like an off duty rookie cop in your 5.11 gear with vest, uber-cool tactical knife in your front pocket and glock t-shirt people will be able to pick you out. Criminals included. I have a closet full of vests. They mostly go to the range now.
I have and wear 5.11 pants for work. I work in the oilfield and 5.11 pants are tough, comfortable and some can be had that are FR rated. Cops don't watch me or follow me around. Remember, Hikers and climbers wore 5.11 (Royal Robbins I believe) way before cops branded the 5.11 with their tactical ninja cop only stamp.