Lots of stuff to figure out about carry. The biggest issue I come to is that I want the gun some places I go and can't carry in others (like on federal military bases, Indian casinos).
I have a Kahr MK9 which is small, 9mm, and sufficient. Most of the time it's in a pocket on the side of the console in the vehicle. I wear a utility vest all the time. It's a standard part of my wardrobe. I carry a wallet, pen, keys, glasses, change pouch, in it. There's a pocket for a gun.
I also carry a portfolio with papers. There's space for a gun in it. This is an "open top" folio, ready access. It's not a "briefcase."
Even a small gun, like an NAA Guardian is a PIA in the vest pocket. The vest is lightweight. The gun is bulky, heavy, and it swings around. 9mm is even worse. In the portfolio things work nicely. I can remove a coat, vest, no bulky shirts. I'm not "wearing" the gun, but I have it with me.
But what I "do" provides me with options. Wearing the vest is a normal function for me, as is carrying a folio. It's as normal as can be for me. It might not work at all for you.
I have a Kramer IWB for the Kahr. It's a nice holster and works well under even a sweatshirt or sweater. But it won't work for a tucked in shirt without a coat or vest. That limits options for taking off the coat or vest. The folio allows removal of coats, vests, etc. And I can discretely secure the folio when I'm someplace . . . drawer in a desk, under the desk. I don't check it in at a coat check -- like at the casino.
If I leave the gun in the car, like at a casino where I can't carry, I lock it in the trunk.
I think the solution to effective carry is to develop a lot of options. I've carried -- effectively -- a sub-compact 1911 and a couple extra mags, on the belt in a pancake holster with mag pouches. But that requires a fairly heavy jacket that's not going to be removed, or a large sweater, sweatshirt. When it works, it works, but it's a pretty limited way to carry.
The NAA Guardian in a pocket holster works in a jeans hip pocket -- if you're not carrying your wallet in your hip pocket. But I stopped carrying stuff in my pants pockets when the wallet made my leg fall asleep. That's when I started wearing a vest (like a fishing vest, only "utility") or a sport coat, for a wallet, keys, glasses, and the "baggage" that I need with me.
One last thought -- these days I think it's possible to carry a small gun on the belt and have it look like a cell phone, or "multi-tool" -- Depending on what you do in life and how you dress, If you're "casual dress," a pouch is a common item on a belt. More formal dress and you have the option of a jacket and a folio. Or you can be "eclectic" like me and wear jeans, sweatshirts, light boots or jogging shoes, and have a vest full of items along with a folio because that's how I work, as a "field researcher."