When I first tried these one my heart fell. They really felt very very tight and it was my usual shoe size. Fortunately, I realised that the wonderfully supportive (and they are, wonderfully supportive) insoles were to blame. I swapped them out for slimmer insoles from Boots and the boots fit perfectly now, even with thicker socks. After they stretch out, and the weather gets warmer, I may swap Teva's original insoles back in again as they're really quality insoles. Right now they're making my Hunter boots even more awesome. Looks wise, I bought these as I have very slim ankles and felt the higher shaft would make the boots work even with thin tights. they do. They work in a cute, rugged, Summer Glau in Serenity way. Absolute love. I finally have the perfect boots to go touring in during Winter.