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My first ever pair of Tim's. I gotta say after two days of wearing them it's painful asf on the inside of my ankles. Does it normally hurt to wear them in? :
Does Timberland boots HURT your ankles? - QUICK FIX - YouTube
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Help] Timberlands hurt my ankle, any suggestions on how to fix it? : r/Boots
Wear This, Not That - The Timberland Look Minus the Bunions | Anya's Reviews
Advice on how to fix this? It's digging into my ankle bone even when wearing high socks. I've seen replies from other posts about breaking them in but has anyone fixed it