As mentioned above: In Florida, this is nearly every day carry. Hawaiian shirts work well here, as there are many tourists that wear them.
Fanny packs don’t work any more. Since 9-11, the theme parks, and many other venues including some banks, stores, and movie theaters, routinely search bags and purses. The default answer for people found with guns is, “go leave it in the car.” Carrying on the person avoids the hassle.
Here in GA it’s almost summer everyday like in FL; fanny packs are not only banned or inspected in many places, but also screams “potential gun” to even the minimally aware– kind of like the ridiculous safari vests that I see instructors and students wearing in even very good gun courses.
My first carry rig was a Rosen ARG (Ayoob Rear Guard), an IWB and I haven’t looked back. I often wear a fly fishing shirt or polo untucked over my current rig (a Rosen USD II Slimline– I like leather), and think it’s essential to resist the temptation to go to the vest or etc. and train in this carry mode: yeah your times will be a little slower but are you training for time/score or to defend yourself?
If I’m wearing cargo shorts I usually have a pocket pistol as a backup, but lately I’ve been doing a lot more pocket carry as a primary gun. The pocket gun advances recently have increased our options.
Michael’s Executive II IWB (theholstersite), loose fitting shirt worn ‘out’, Perry suspenders (worn under the shirt) to help keep pants or shorts were I want them and me and my SP-101 are good to go everyday, year round out here in TX.