Depends on what you're doing. If you're wearing spurs, you'll want tall leather boots, and if you're rope climbing branches, you'll want something with some flexibility for good footing on the branches. I used spurs very little in my tree business because I was mostly pruning and doing large branch removals. Spurs were only useful for me on pines if I was taking out the whole tree. In both cases I wore Red Wings but that was 30 years ago and I'm sure things have come a long way for tree climbing boots since. Be safe.