I bought these boots for 2 reasons: 1. I wanted a black wedge boot and 2. I love Jessica Simpson shoes.  These definitely ROCK!  The day after they arrived, I wore them a full 8-9 hours and they didn't cause one bit of discomfort.  Living in downtown Chicago, you walk everywhere so a comfortable boot is a must....these are perfect!  They fit true to size, but if you're looking to wear thicker socks, I would get a half size bigger. I typically wear thin trouser socks and they fit very well with them. They are a slouchy boot, but the "slouch" holds up very well. Mine are quite high (just under my knee), which made me even happier.