I wear jeans most every day, and either a T-shirt or T-shirt and Fleece sweatshirt. Anything different is rare.
With that in mind, I wear/carry the following right now:
Frank Proctor/WOTG belt
Springfield Range Officer Compact 9mm (8+1 with Federal 147gr HST) in a Vedder AIWB or a full-size 1911 in a JMCK Wing-Claw
Spare magazine (10+1 for the 9mm, 8+1 for the .45s) carried AIWB opposite the pistol
Ruger LCP in right front pocket (my "always" gun that goes in the pocket when I dress in the morning and doesn't leave until I go to bed)
Utility knife (CRKT Squid) clipped in right front pocket
Surefire Stilletto flashlight clipped in left front pocket
Cell phone in left front pocket
Badge wallet and general wallet in back left pocket
right left pocket is left empty to put keys if I'm in a store, etc.
Ryker Nylon ankle med pouch with SOFT-W, combat gauze, chest seals, shears, gloves, and a AAA FourSevens light
the Ryker med pouch took a couple days before it was comfortable and not ridiculous, but now I don't even notice it and carry it everywhere.