Well I'm not a great believer in waterproofs for cycling, and find the windproof fleece type jackets to be somewhat water resistant, and up to a point you don't really get that wet inside as your body heat keeps you dry. Once you'rr in cycle-specific clothing, if you get a bit damp it doesn't hugely matter.
I've got a very nice Assos one - 851 I think was the model, and though by no means cheap, wasn't absurdly pricey as there was a deal on. I've also got an
Altura night vision fleece (not their similar looking and named waterproof coat) - which though not nearly .as "nice" as the Assos is almost as good in truth. All the usual makes do similar kind of stuff.
I wear 3/4 length bibs most of the year, sometimes with long socks, but I also have a pair of proper full length "winter drawers on" in Roubaix material when it's very cold - though I find them a bit restrictive and don't wear these much.
Good gloves very much matter. I've got some cheap Atura semi waterproof ones, sadly nearly worn out, and a pair of seal-flipper Assos overmits, windproof gloves and inners - again on special as a set of three though still quite expensive. These are great. I still recall the pain of a forgetting gloves day over 30 years ago !
Shoes - well if you're using toe clips or flat pedals, then whatever you like. I used to favour my best Loake brogues, but if clips ins (a very good thing), then that's a whole different set of choices.