I had never even tried on a FitFlop shoe/boot before I ordered these boots. I ordered one size down, and still was able to insert my orthotics with no problem--still had plenty of room. They fit great in the calves and ankles (I have somewhat heavy calves) and hardly needed any breaking in. Easy to pull on and off. These boots are very stylish, and wonderfully comfortable to walk in. I will definitely order more FitFlop shoes!