I've gone off the deep end completely and just wear my outdoor gear all the time, stuff similar to this if it's cold and/or wet or regular 100% polyester pants and running shoes if it's dry.
If you need waterproof shoes then just look at getting hiking or walking shoes that have Gore Tex. Salomon is a good brand, I have a model similar to these and they're bulletproof, but they're pretty heavy and have no flex at all so they're better suited for softer terrain.
I'm going to grab a pair of terrain running shoes for my next hike, that's my recommendation if you walk a lot and need waterproof shoes, but it all depends on how much of a doofus you're comfortable with looking like, but again, I've almost completely stopped caring about what other people think about me at this point. If other people think I look like a dipshit then that's their problem, I dress for myself and not to please other people.
https://www.salomon.com/int/product/x-ultra-3-gtx.html?article=398668 