Could you recommend some winter dress boots that are stylish and waterproof?
No, Jeremy, I will not recommend you a dress boot. Because you are not Errol Flynn and this is not the Spanish Main. What you need is a practical pair of rubber Wellingtons, which allow you to march to work through slush ponds without so much as breaking stride.
However, if you are friends with Errol Flynn, you can wear a monocle and roll your r’s while singing Garry Owen.