You can't rework a classic. Or, can you? By adding extra height to its Cruise boat shoe, Sperry proves that you can extend a summertime staple, adapting it for fall and beyond. Here, the familiar silhouette features a taller, high-top height, plus lacing and a traction outsole. The result pairs just as well with jeans as it does shorts, and gives him something that's both playground and boardwalk ready.