1. What shoes do you wear when riding?
Reebok Classics (for the most part in not too picky at all!)
2. How long would you say they last?
Forever they generally go from the top first, so they only get ruined from proper nasty ass over tit bails.
3. Whats the ankle support like/is there any?
They cut off just under the ankle, but they do help to prevent ankle roll to a certain extent but not entirely
4. Soles: grippy or not that grippy?
Grippy'ish... depends on loads of factors, pedals, blah, how new they are, but with cage pedals the toe is a perfect fit for a platform, perfect sole, hard but not too hard.