I've had a ton of success with a simple fix. I used to spend 200+ a pop for period-looking boots, but for hours of NPCing, they didn't last and weren't as all-weather as I'd like.
Then, I got gaiters - specifically, Swiss Army Leather Gaiters. (My second favorite creation of the Swiss Army...) These cover almost any standard black boot, look neutral for any character, and the buckles hold fast and look period.
For the most part I've found high quality leather hiking boots to be the best compromise of durability and "in-period-ness". I've been using a pair for years and they're only now showing slight signs of wear after all the abuse I out them through. Of course they're not as in period as some other boots but for 80-90 dollars cheeper and some water proofing it's well worth it in my opinion.
I use military all leather speed lace boots as my best compromise. I have been wearing the same pair for I think five years now? This is both as a PC and NPC, and even general everyday wear and they're just now to the point of too much damage that I need to replace them.