24. Osiris D3 (2001)
Yes, skateboarding shoes matter too. Osiris dropped just about the heaviest shoe possible in 2001 when they released the D3. The shoe had more tech in it than any skate shoe to that point.
While breaking ankles is more usually associated with basketball, you move wrong in these shoes and these bricks will break your ankle. This style is making a comeback too with A$AP Rocky and Under Amour basically ripping these off with their own release.