You want traction when you're navigating the slippery slush and classic rubber-soled boots (Red Wing, Chippewa, Wolverine) will keep you rooted to the sidewalk.
Treat your pair with a leather protector spray like Kiwi's Super Protector, $9. It blends into the leather without giving it a cheap sheen or altering the color.
You should be wearing thicker socks like a pair of wool camp socks that not only add some cushion but keep you warm.
If you made it through the fall without a pair of rugged boots, allow us to make the case for them now. With the revival of all things Americana, there's no better shoe to sport. It's fortuitous then, that they're also just what you need to survive the cold, wet season ahead of us. But you can't expect them to stand up to the brutality of winter if you don't treat 'em right.