Anna Wintour looked quite the chic cheerleader last night. Poised next to Rupert Murdoch, she watched her favorite Fashion Week buddy, Roger Federer, battle it out against tennis hero Pete Sampras at the sold-out Madison Square Garden. In fact, an assortment of celebrities —Tiger Woods, Chloë Sevigny, Regis Philbin, and a fresh-from-court Barry Diller —showed up to watch the dashing Federer and the legendary Sampras fight it out on the court. But while the two tennis greats were fierce during the game, they were friendly before, during a Q&A session in front of a VIP crowd in the NetJets private lounge, where they compared Wimbledon wins, private-plane experiences, “favorite strokes” (they both like their serves), and training schedules. Federer says he plays for four to five hours a day, in addition to body conditioning and routine massages. “Yeah, it’s pretty much the same for me,” the now-retired Sampras agreed, then paused and said he was kidding. “To be honest, I get bored after about an hour." When asked if he had any advice for the reigning champ Federer, Sampras smiled: “Sure. Quit now.” Then Federer beat him. —Katie Goldsmith
Anna Wintour's crush on Roger Federer extends to sending him expensive clothes, reports "Page Six." (The Post gossip column also coins the phrase "comely cougar" to describe the steely Vogue editor, which is just so catty and, you know, accurate.) But a Condé Nast rep protests, "Vogue certainly helps a number of people with fashion, but Roger's style is all his own." We have to beg to differ on this one. The fashion bible has repeatedly featured Federer, dressing him up in all kinds of outrageously luxe clothes. In one Men's Voguespread alone (shot by Annie Leibovitz), Wintour draped Federer in over $4,000 worth of Prada, $2,500 worth of Gucci, $1,500 worth of Dolce & Gabbana and Michael Kors, and $2,500 worth of Dior Homme. Since much of that shoot took place at sea or on the beach, it wouldn't be outrageous if some of the clothes didn't get returned to the designers. Not that we object — handsome men deserve to wear expensive clothes. We're just wondering whether Wintour has taken to calling Federer "my pretty" yet.
Roger's Stylist [NYP]
Earlier:Roger Federer Makes Anna Wintour So Very Happy
Alice + Olivia designer Stacey Bendet took offense to Molly Sims's comment that the label was "lower end" by claiming that Sims begged for free pants and a plane ticket to the show when she modeled for her last February. Tennis stars Novak Djokovic and Maria Sharapova claim to be just friends, but they were out singing karaoke together till 5 a.m. the night after Djokovic lost in the finals. In other tennis news: Some designers were annoyed that Anna Wintour spent more time with Roger Federer at the U.S. Open than at Fashion Week shows. Details editor Dan Peres is expecting his first child with Aussie wife Sarah Wynter. Walmart competitor the Wholesale Department Store Union bought out a showing of Off Broadway show Walmartopia. Chef Todd English, of Olives fame, may open up a new place on 98 Kenmare Street. Liz Smith's sources tell her that Rudy Giuliani is "a bad man and an erratic personality" but would make a good chief executive.
Anyone claiming to be unmoved by the Oscar de la Renta show is a liar. No matter what your take on his clothing is, the setting — at the Third Church of Christ Science on Park Avenue — was frankly kind of spectacular. Add to that an exuberant live performance from the Polyphonic Spree (who surely could never have predicted playing for a roomful of uniformly blonde Upper East Side matrons) and a spontaneous standing ovation for U.S. Open champ and the future Mr. Wintour, Roger Federer, and you’ve got yourself a hell of a morning.