David Bowie used to be the ultimate androgynous sex symbol. He dressed up as Ziggy Stardust. He pranced around in an orange-red mullet and moon boots. And then ... he got old. But while most rock stars age ungracefully, Bowie went in the opposite direction: he got cooler. Now married to former supermodel Iman, Bowie looks like a real-life Don Draper. He wears dark sweaters and pinstripe suits, and his age-appropriate hair is short but still trendy. What can we say? The man looks good.
Top 10 Celebrity Makeovers
In honor of Willie Nelson's "haircut heard round the world," TIME takes a look at other stars whose appearances have transformed over time