Anna Wintour is no stranger to the tennis court, but last night she sat courtside at the Knicks-versus-Cavaliers basketball game in Madison Square Garden. She was there to, um, purse her lips at her latest cover model, LeBron James, who "Page Six" reports will appear with Gisele Bündchen on the cover of Vogue's annual shape issue in April. We're going to resist the obvious Federer jokes here — but Wintour knows how to match her sport. Last night homegirl dressed down — we're talking jeans-tucked-into-flat-boots down. We can't recall seeing Wintour wearing slacks, much less jeans. Take a look back at the tennis-match outfits she wore to the U.S. Open after the jump.
Cover Boy Chic [NYP]