Sorel Caribou Boots

Who: Justin Timberlake

Timberlake has been known for supporting Nike and Jordan Brand on a regular basis, never trying too hard or anything over the top — just a steady rotation of clean classics. When JT was caught on set with Cameron Diaz rocking Sorel boots it wasn't exactly the former-N'Sync frontman's best look — unless there was a blizzard coming. Far from bringing sexy back, homie.