9. Airwalk Prototype
Some might consider the Airwalk Prototype the first "real" skateboard shoe. Others, most notably people at Vans, may tend to disagree. But the bulky Prototype melded classic skate shoe board feel with the armored upper of a basketball shoe, which many skaters found themselves rocking when the money dried up. Airwalk went on to produce a whole "Prototype" line with all kinds of add-ons, but the first one was perfect.