How to Wear Ankle Booties with Socks - give your jeans 2 little rolls (Madewell Skinny Jeans: Rip & Repair Edition), slip on thicker camp socks (J.Crew), bunch them up, & tuck them under your jeans, slip on ankle booties (Sam Edelman - Lucille in whiskey)
This often occurs in overweight, middle aged women and men as a result of degenerative changes in the tendon. The rupture may be partial or complete with pain below or behind the inside ankle bone (medial malleolus). A flattened arch is common. Anti-inflammatory treatment (physical therapy modalities), orthoses, and surgical debridement are common treatments.