michael-jordan-man-of-style
See All Photos Chad Hunt for InStyle

In 1996, two years into its existence, InStyle debuted its first-ever Man of Style, a feature that still continues to this day. Michael Jordan was our inaugural interview, and the basketball superstar shared with us his sage thoughts on wearing suits (and why he owned anywhere from 100 to 150 of them). “They let people know I’m serious,” he told us. “My father always said, ‘Sometimes people’s personalities can be defined by the way they’re dressed—or the way they smell.’ And I take that to heart.”

Over the years, we’ve learned that Jordan isn’t the only dude to be a bit of a clotheshorse (or to at least have definite opinions on the matter of style). As we get ready to celebrate our 20th anniversary, we’re taking a look back at the variety of men we talked to for the column—from music royalty like Sir Mick Jagger, Jay-Z, and Bruno Mars, to Hollywood’s hottest, including Bradley Cooper, Hugh Jackman, and Ryan Reynolds—about their inner fashionistas.

Here are a few of our favorites, plus find out how you can be a part of the 20th anniversary celebration with us.

MORE:
InStyle Is Turning 20! Come Celebrate With Us
20 of the Most Gorgeous Red Lip Looks in 20 Years
What the Winners Wore: 20 Years of Best Actress Oscar Dresses

—Jeryl Brunner