Shoes: good for a few outings (really nice on snow) but then lose their water repellency. If you have sweaty feet, your socks will get wet from sweat anyways. Just bring extra socks or wring them out periodically. Wool socks will feel warm even when wet.
Jackets: great in a downpour but if you're wearing pants, all the water just rolls off your jacket and soaks your pants. Use a weather forecast and just don't go or choose another location if it's going to be pouring out and instead settle for a much lighter water repellent layer for 100s of $$$'s cheaper that works in a light rain or snow. I use the OR Helium. Packs real small.
Otherwise, if your job requires you to stand in the rain all day, definitely invest the $$$.