![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? : 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? :](https://i.redd.it/yirb8smg9uca1.jpg)
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? :
![Amazon.com | Timberland mens Tillston 6 Inch Double Collar Ankle Boot, Pure Cashmere, 8.5 US | Chukka Amazon.com | Timberland mens Tillston 6 Inch Double Collar Ankle Boot, Pure Cashmere, 8.5 US | Chukka](https://m.media-amazon.com/images/W/IMAGERENDERING_521856-T1/images/I/71OJ-o80BtL._AC_UY1000_.jpg)
Amazon.com | Timberland mens Tillston 6 Inch Double Collar Ankle Boot, Pure Cashmere, 8.5 US | Chukka
![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 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](https://preview.redd.it/ug47rgr45hz51.jpg?width=640&crop=smart&auto=webp&s=ef0eb4e1e30e43ef78e1d4af03a89c4202e93b76)