i don't know..i am more seeing this with a cute wedge or something like that. i'd have to see the boots. maybe red ankle boots with a simple sweater could be nice...
I think the silhouette could be unflattering. If that skirt hits below the knee, there may not be any leg showing before the boot. That could make the legs look bulky. Likewise, if you wear mid-calf boots, the widest part of the calves would be bare-legged.
Ankle boots could work, but I too am seeing more a wedge or ladylike pump with that skirt. It is REALLY cute!