I have the Keenland, which I think is like Highland but shorter shaft (has that same medium heel, ties, goes to mid knee on me). How it fits your actual foot is probably the most important, I had to size up as the style I got runs narrow (and I have fairly narrow feet, many shoes are wide on me), usually I wear a 10, I bought these in 11, sometimes I do need 11 in a closed shoe though so might be true to size? They are much easier to put on if you wear socks, I'm glad I got the bigger size so I can wear fuzzy socks. I consider myself thin, like a size 2-4 at 5'7" and thin to average legs, the shaft is not tight on me, I can easily wear skinny jeans under but they aren't too loose to go bare legs with a skirt too. The ties help them stay up. If you wear a smaller shoe size the shaft will likely be much smaller though as typically this is proportional.