I would think a pocket holster in the jacket pocket or pants pocket for church. I wear jeans to church with an un-tucked shirt so AIWB works for me.
The shield might be a touch heavy for basketball pants.
I have a stealth gear holster, I hear good things about the alien gear.
For basketball pants, look into a belly band. But make sure it’s a high quality belly band that keeps the gun secure and protects the trigger area.
Alien Gear Holsters, they have a good warranty and are rather inexpensive.
My body and clothing choices allow me to often carry with my favorite holster, an OWB paddle Blackhawk Serpa holster, most comfortable and secure holster I’ve ever had.
Cant, just a lot of trial on that. Ammo, Hollow points always, I personally like Hornady with Flex Tips.
As of right now, I have my M&P Shield 2.0 9mm…
Great choice. If you are still undecided on your ammo type, you have LOTS of great options. My recommendation would be Federal HST or Speer Gold Dots in either 147gr or 124gr. Hornady and Winchester make some great ones here too, and then you also have some smaller boutique ammo companies making good stuff (altho for liability reasons I’d choose one from a major brand). Luckygunner has a great compilation of data if you like numbers. Shooting The Bull on youtube has a great set of tests, and his final conclusion is here (as of May 2019). For a greater understanding of terminal ballistics in general and covering a lot of other calibers, this (slightly dated) article over at ar15.com is excellent.
most of the time I’m in an untucked, button-down dress shirt(work)
You’re right, this is the easiest 
Any carry position at your waist should be good to go. You could maybe even go OWB in the right shirt.
suit and tie(church)
You can still go IWB or AIWB as long as your holster is tuckable. In fact, the tucked shirt “poofing out” over your belt line helps hide a lot.
If you carry appendix people can easily see the front of your pants with the jacket open, they may or may not notice the holster clips. Snaps are less noticeable (especially with a leather belt the same color), J-clips even less noticeable, and ulti-clips are even less noticeable than that.
You can also go with shoulder carry, or OWB strong side. Both of those may be visible if you happen to reach high for something or otherwise move the jacket out of the way temporarily. You could also pocket carry altho the Shield is probably a bit too big IMO for pocket carry, so you might need another firearm (as good an excuse as any to get another one ).
basketball pants and t-shirt(everywhere else).
Basketball pants are hard. If they have a solid drawstring you might be able to use ulti-clips to attach the holster to the pants directly (since there is no belt). I’d worry about the weight pulling them down tho. Again, maybe an excuse to get a firearm that is even lighter 
Otherwise I think a belly band would work great here.
Your last choice here would be off-body in a sling pack, fanny pack/utility belt, backpack.
^^^^^ THIS!! I went for too many years wearing whatever kind of belt trying to keep a stainless Colt Officers Model in place. I ended up with a Bianchi B21 contoured bet. The difference in carry was HUGE and the difference in draw was even more profound. Nothing like draw practice where you have to hitch your britches up before each draw. Draw and Hitch, Draw and Hitch (add in Jeff Foxworthy voice from Cast and Tug).
For dress I ended up somehow (I honestly don’t remember how I got it) with a 1" Blackhawk gun belt in “carbon fiber” design that, while not as stout as the Bianchi, was much better than any dress leather belt I ever had.
Cheers,
Craig6
A good belt yes, my belt it a reinforced work belt From Walmart, inexpensive and sold enough to last years of abuse. My current belt I’ve been wearing for years and I would estimate it has at least 6 months left of life to the stretching of the holes in it…
I’m afraid the initial question is way too open ended. What works great for one person my be totally unworkable for another. You “will” need a good belt, then proceed from there with weapon type, size, how you dress and where you want to carry and what YOU feel is a safe carry method. Read Everything you can find. Oh, you Will wind up with a box of holsters. If at all possible, try before you buy, it will save you $$
The most important thing I can tell you is set aside as much money as you can afford for a training budget and seek as much training as you can get from qualified instructors with proven programs.
Being both an NRA and USCCA instructor that’s the two I can recommend without qualification but there are others out there.
Beware, though “tacticool” and “street warrior” mentality has become epidemic and there’s a whole lot of folks out there peddling pure BS.
No private trainer is going to make you into an invicible Navy Seal or Army Ranger no matter how good a line of BS they are peddling.
We have a whole lot of hard evidence and stat’s that show us what kinds of self defense scenarios are common and those are the one’s to train for.
My training priorities are simple.
Spend 70% of your time on the most common.
Spend 20% of your time on the less common.
No more than 5-10% of your time on the least common.
We’re not cops, we’re not vigilantes, the odds of you ever being in a deadly force encounter to start with are pretty slim considering our ever falling violent crime rates.
The most common such encounters you are likely to face are a home invasion, a parking lot robbery, a car jacking, or being an innocent bystander when you are in a business that is targeted for an armed robbery.
Learn good situational awareness, learn what to look out for, how to always keep a plan in your head leaving yourself as many options as possible and don’t do stupid things.
Lean conflict avoidance and deescalation techniques.
Avoid escalating conflicts such as road rage incidents. Does it really matter if you had the right of way and some jerk cut you off if you end up with a bullet in your head or your family gets shot up because you gave someone the finger and honked at them for cutting you off? Your’e just as dead and so are they whether you are right or wrong.
One of the best aspects of Joining the USCCA is the constant stream of good quality training materials that are made available to us for free. Make use of them, study them, and if you can get out and take the USCCA classes. No matter how much or little experience you have they will benefit you.
Another outstanding resource I can highly recommend is The Active Self Protection Network on Youtube.
Every day John will put up at least one new self defense scenario that has taken place, he breaks them down and evaluates what was done right or wrong or what could have been done better even if it wasn’t wrong.
He pulls these videos from all over the world and does an excellent job of giving you an accurate and unbiased breakdown of what went on.
You can join for like 4.00/mo and it’s absolutely worth the money.
Even if you don’t post actively/regularly here this forum is a very good source of information as well. We won’t all always agree but even when we don’t we have valuable discussions.
Ain’t this the truth.
@WildRose, that was the best reading on USCCA Forum.
Your post should be used as Welcome for new CCL owners.
Good job sir 
Well said! FAR too many armchair commando’s out there who talk like they are going to war, not to everyday life. Funny thing, when you run into ‘em in the flesh ( usually at a LGS) and they’re mouthing off about their .50 DE “edc” (or similar cannon) and related tacticool gear that “you have to have”, they almost never are actually carrying their portable howitzer “that day”
. The little .22 that is ALWAYS there is a far far better defensive weapon than the cannon that’s at home because it’s “too heavy”, too hard to conceal”, or “too uncomfortable” to actually carry ALL the time. Do your homework, find what works for YOU, and go with it. Good luck and stay safe!
Don’t get hung up on the caliber, ignore bashing on .380, .32 etc.
Don’t forget about a backup, whether it is edged or club-type.
Maintain your physical form.
This reminds me of a quote, @Dwayne: “Concealed carry is not supposed to be comfortable. It’s supposed to be comforting.” - <Can’t remember who…>
Jeff Cooper?
Not sure, but I did a search on Jeff Cooper and found a “25 Best” site. Here’s my favorite:
"One of the notable aspects of the democratic process is that one need not know anything about a subject in order to pass laws about it.”
Thanks for the introduction to this clear thinker, @Dwayne.
Alex
Clint Smith
Col Cooper was a true American. Glad you got introduced👍
Thank you, @Jerzees! He’s got quite a resume.
This rings true because I’m certain I heard him being interviewed on the Guns Magazine podcast about Thunder Ranch. I’ve been listening to them on long drives.
Thanks all,
Alex