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Amazon.com | Timberland mens Tillston 6 Inch Double Collar Ankle Boot, Pure Cashmere, 8.5 US | Chukka
Amazon.com | Timberland Women's Nellie Double Waterproof Ankle Boot,Wheat Yellow,5 M US | Ankle & Bootie
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
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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? :
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