You know it's time for new ones when:
The insides look (and smell...) much worse.
I've gotten every penny outta these guys over the past few seasons of local chunk, regional bikepacking, and all of the ding-dang off-bike hiking involved in trying to be a photogeek.
And yes, I already snagged another pair. Downright cheap IMO.
Awesome shoes--comfy as slippers with none of the BS buckles or carbon or other assorted viagra that non-riding magazine editors tell you you need.