A stretchy panel—like the one on this wedge from Rockport ($225)—gives you the flexibility you need.
This leather knee-high by Ayla is one of many customizable designs. Send the company your measurements, and they'll build you a boot for $200.
Fitzwell's boot ($169) builds in extra space where it's required, narrowing at the ankle for a sculpted effect.
A low-heeled boot ($79) from Silhouettes, specialists in wider styles, proves color won't make calves look bigger.
Some labels offer extended-calf sizes for a few bucks more: This J.Crew leather and suede boot ($345) has cool equestrian details.See more styles in O's Ultimate Boot Guide!