Wintour and Federer, all smiles at the Oscar de la Renta show on September 10.   (Photo: Patrick McMullan)

There is so much that fascinates us about Anna Wintour: the shiny shell of her iconic bob, the way she flees from fashion shows like Satan himself is nipping at her heels, how she baldly refuses to paint her toenails an actual color. But in the last year, the best tidbit we’ve gleaned about the coolest person on fashion’s front row is how completely she thaws for tennis ace Roger Federer.

Since she started squiring Federer, 26, to several marquee fashion shows in the past two years—like Marc Jacobs’s in September 2006 and, most recently, Oscar de la Renta’s spring 2008 presentation in New York—everyone from the front row to the cheap seats has been giggling about how a woman who once dated much older men suddenly has a new boy toy (she’s 58). Thanks to the overlapping schedule, Anna frequently trades bits of Fashion Week for Flushing Meadows, especially during his matches. She slapped Roger’s sexy mug on the cover of Men’s Vogue. And she confidently allows his girlfriend to tag along on her and Roger’s post-victory Fashion Week forays, as if to remind the poor girl to lock him down fast, or pretty soon she’ll be reduced to weeping into the miniaturized Wimbledon trophy he’ll leave behind as a souvenir of their time together.

Not that we blame Anna for being all over Roger like the head cheerleader on the star quarterback. The guy is gorgeous, erudite, multilingual, and capable of hitting a tennis ball faster than most people drive. And it’s certainly logical that a woman with an unerring eye for trends would be similarly blessed with great taste in man-candy (bonus: It’s always in season). Still, it’s tremendous to see that the tough-as-nails editrix—she unabashedly wore Prada to the premiere of The Devil Wears Prada—actually has a mushy, marshmallowy center.

Maybe she’s grooming him for her lovely daughter, Bee Shaffer, so she can still pinch his bum at family gatherings without being tied down (just in case Federer’s muscular foe Rafael Nadal shows a keen interest in being the next Mr. Wintour). Maybe, as an avid tennis player herself, Anna merely respects a guy with wicked topspin. Or maybe, and we would agree with this wholeheartedly, Our Lady of the Dark Glasses just wants the person who rubs her feet at night to look wicked hot in a towel while he feeds her grapes from a Blahnik-shaped bowl.

If that’s the case, though, she’d better get cracking on establishing a Sydney Fashion Week that coincides with the Australian Open, or else it’ll be a long, cold Wintour before her annual U.S. Open Federer fix. Failing that, we’d like to suggest Anna find a winter-sport bench buddy as well—someone to keep her warm during February’s fashion shows. The adorable Tom Brady is usually all done with the Super Bowl by then. Watch out, Gisele.