Very comfortable, even on the first day! They display a great, worn in appearance after just a couple of wearings (the leather distresses as you bend in them.) There are side zippers for easy on/off, but the laces allow you to customize the fit to your foot + ankle, providing tremendous support and stability. Pulling the laces up tight on the instep keeps the foot from squishing forward, which means no toe scrunch! BONUS! The heels + soles are strong and not slippery at all. They are also fairly quiet even on wood floors - and add a great "strut" to my butt! I did order up a half-size to allow for socks, and you may need a shoe horn to get them on without breaking the heels down - unless you unlace them each time.