Who: André 3000

What He's Wearing: Hard to say apart from the Jordans, but the OutKast star has shown a taste for Rick Owens and vintage in the past.

Why It Works: Some guys bow out of fashion as they approach mid-life, others such as André 3000 mature like an expensive Gruyere cheese. At 45, Dre might no longer be on his Ziggy Stardust tip from earlier this century, yet his style evolution is proof that dressing for your age needn't be bland. Praise be the rare breed of multi-millionaire who still has personal style.

Filmed hanging out with footwear designer Salehe Bembury, Three Stacks looked relaxed in his favorite military fatigue jacket (by my reckoning, he's been wearing the same piece for about five years now — sick!) and a pair of Js. It’s a straightforward vibe with just the right amount of scruff (we're really digging the beard), and an appropriate look for a legend who has been there, done it, and bodied just about every fit there is.

It's yet another rare public appearance from the rapper, who has cut a merry figure while playing his flute around the streets of Philadelphia, New York, and Los Angeles in recent times. Could a woodwind record be coming soon? Probably not, but we'd take it.