Why do i feel pain under my ankle when i wear my wooden clogs?

Lack of flexability: Wooden glogs are very stiff and don't allow for much flexability of the tendons and ligaments around the ankle.

Pronation, shock: Wooden clogs do not provide enough shock absorption. May think about dansko clogs made from rubber. Pronation due to lack of support in the clogs may cause jamming of the outer portion of your ankle causing pain and swelling. Try rubber clogs if you like clogs and if not better than seek help.