Rap stars didn't come much more stylish than Usher during the late 90s and early 00s. He never seemed to put a foot wrong - even when he went as far as trying an all-white look for his prom night. 99% of people couldn't get away with this outfit in their wildest dreams. Usher is not 99% of people. He's in that top 1%, and he's styling it out here!
His date has risen to the occasion too, with a sleek red dress that matches his rosette. They look like a great couple, but they might have been caught in the middle of a debate here. Neither of them appears to be too happy about being photographed. Also, is it us, or is there a rip down the middle of this photo, like it's been torn apart and then put back together? We hope their evening together was a happier one than this image seems to suggest!