Cooper Flagg’s Boss Moves: Getting Ready With the Basketball Star Ahead of the 2025 NBA Draft

He sounds pretty relaxed as he’s en route to Midtown’s Lotte New York Palace for a fitting with Boss, which outfitted him this evening in a made-in-Italy three-piece suit of deep navy stretch wool and a silk jacquard tie. It’s the first of a few select dressing occasions between Flagg and the label—further strengthening of Boss’s sporting focus. (The company has also partnered with football’s Patrick Mahomes and Cam Ward, and tennis’s Taylor Fritz.)

“I have seen and paid attention to different guys’ outfits—what they’re wearing in the tunnel,” says Flagg. “I’m excited to step up my game and be ready for next year. I think my style, or what I like for portraying myself, is to stay classy, sharp, even simple.” Flagg cites Orlando Magic forward Paolo Banchero’s aesthetic as a good example.

Flagg is known for his all-court game and notable defending power. He was named an All-American athlete while at Duke, and was also awarded the prestigious Naismith College Player of the Year. While he does not call out one specific basketball idol or role model, Flagg does say he’s been inspired by “pieces” of certain player’s games, namely Kevin Durant and Jayson Tatum, and that if he wasn’t in the arena, he’d likely be playing golf (he’s a 14 handicap, and improving).

As for his high-intensity drive? He attributes it to something those of us with brother and sisters might all recognize: good old-fashioned sibling rivalries (Flagg has a twin named Ace and an older brother named Hunter).

“My parents taught us to just put everything into it that we had—to just give it a hundred percent all the time,” says Flagg. “And that came down to just being in the driveway with my brothers, playing one-on-one. We were having fun, but we were really competing.”