The Air Jordan XI “Concord” is slated for its fourth retro this weekend. One of the most popular silhouettes from the Jordan line, the sneaker features a patent leather rand that wraps the foot and takes design cues from men’s formal dress shoes. Drawing from both the world of high-level performance and fashion, the Air Jordan XI was one of the first models to blend the two different aesthetics.

With its sharp white upper and black patent leather toe box, the XI even became a statement piece to pair with more formal sartorial choices. From high school proms, to weddings, to the red carpet, the sporty-yet-classy look has become synonymous with the shoe in the 20-plus years since its introduction.

For its upcoming re-release, we asked prominent men’s stylists what they think of the aesthetic, and to review the outfit choices of those who’ve taken the XI outside of the gym. John Tan, who’s styled the likes of Ansel Elgort, chimed in with his take on the suits-and-sneakers look.

“I think it can work depending on the individual and how it is paired. I love the idea of a classic suiting look, and then add some individuality with an interesting pair of sneakers that stands out,” Tan said. “Most guys want to be stylish but comfortable, so the right pair of sneakers can be a cool alternative to a pair of dress shoes—depending on the event or occasion.”

To go more in-depth, we asked style expert and author, George Brescia, as well as Los Angeles based stylist and managing editor of Detour Magazine, Jeanne Yang, to comment on a few specific instances of the look. Check out their takes below on these celebs, suits, and sneakers.

Whether you’re looking to pick up the retro colorway for shooting hoops in the gym or for walking the red carpet, the sneaker drops this weekend, Dec. 8 for a retail price of $220 on the Nike SNKRS app and at select retail locations.