You might want to do the treadmill instead of the street for first jogs. The absolute consistency of the surface will keep your ankle from doing anything out of range. Also its give cuts down on the jolt.
Plus, if you decide to quit,,,, you are already home, or the gym or wherever!
I'll vote road... easier to speed up/slow down quickly if the ankle complains, with lower risk of falling of the treadmill while doing so... I've certainly always felt a lot more stable/in-control on roads, than on treadmill, when recovering from ankle injury.
Opted for just the road, doing a loop that kept me close by since I don't have a treadmill at hand here in Boston.... and ok, I think, certainly I don't have full range of motion for dorsiflexion, but PTing for that a few times a day! And will see what sports doc says on Tues.