The reason behind Timberland boots or any boots hurting ankle means that the boot hasn’t broken in properly. It could also mean the ankle area hasn’t been laced the right way. For a quick solution, you could speed up the break-in process or stretch the leather. 

What’s not to love about a pair of UGG boots? These are comfortable boots that have the extreme durability of sheepskin leather. And not to mention, these have timeless designs. …