Anna Wintour Unveils New Look — Jeans! — for New Sports Cover Boy

On the left, Wintour attends the Open in a lovely red dress with extra-blonde summer hair and a surprising choice of footwear on August 28, 2006. On the right, Wintour at the Open on September 7, 2005, looking as though she dropped her badge. Photo: Getty Images

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]