For year-round, I’d say a brown pair of wingtips. If they’re blucher style, then they’ll be casual enough to go with denim, while still perfectly fine for going with a suit. I think my wingtips are fairly versatile to wear with almost anything in my wardrobe. Get a pair of overshoes and you’ll be set for light snow and average rain, too.
For winter, I thoroughly suggest not fucking around and getting a pair of L.L.Bean Boots. When it got crappy out, these were my default, go-to shoes. I will note, however, that I kept a pair of “normal” shoes at the office to change into and wore the boots for commuting.
If you want something more classy for winter, a pair of military or brogue boots with a Dainite sole (or lug sole if you feel so inclined for a more rugged look) will do you nicely, like the Charles Tyrwhitt pair I mentioned. I’d also take a look at dieworkwear’s guide to rainy-day boots. Those Brooks Brothers shell cordovan boots are amazing.