I have black suede ones that I wear with tights (coloured or boring black) and a long jacket or dress. I bought them in Summer so also paired them with Denim shorts, but I had to wear Rescue Tape (Lincrafts version of Hollywood Tape) to keep them from falling down.
I think as long as they're not leather and massive healed, they look hot!
I think they'd look nice with skinnies and a blazer or a cape. Saw a girl wearing knee high boots and it looked really stunning with a simple white button up shirt, blazer and jeans, hair pulled into a high bun.