99. Creative Recreation Cesario
Creative Recreation AKA Creative Rec pushed brands when it jumped on the scene in 2002, and the Cesario was the Bentley err, Chrysler 300 of the models they put out. The sneaker had a high-end look at a price you could afford. Thanks to its ability to blur the line of a sneaker and legit grown-man style, the Cesario was a shoe you could rock to the club without fear of getting bounced at the ropes.