You could look into shoes that are geared towards waiters/waitresses. They’re typically designed to be slip and water resistant, durable, comfy enough to wear while moving around for hours, and you can find them in varying levels of formality in order to blend in with the restaurant’s style. Skechers and Dr. Scholl’s have some affordable options, but they may lean towards the more business casual rather than the dress shoes end of the spectrum.
The IFAK article was a huge help for getting started and showing me what to prioritize. Up until now I’ve just tossed whatever I had on hand into a ziploc bag for camping or hiking trips. It might still use a plastic bag in the future, just for water proofing, but I’ll definitely be a bit more intentional about what I’m putting in there. I’ll look into a small hard case for the meds, and I might pick up that Fox Tactical pouch if I decide to put together a second bag, thanks.