Rafael Nadal   (Photo: Nigel Parry)

Playing it safe: not something our cover model, Rafael Nadal, does, either in the way he attacks the net or in his singular on-court style (the No. 1–ranked male tennis player in the world wears Capris). The same can’t be said of this season’s somewhat conservative turn: three-piece suits, leather jackets, slim pants. To make the most of it, we gave photographer David Benjamin Sherry, known for his intimate, unguarded pictures of his bohemian friends, a pile of designer clothes and no directions other than to hang out with them for three weeks. The album that came back starts here. We asked cartoonist Jim Rugg, who’d never written the name “Martin Margiela” in his life, to imagine a fashion story; he created a twisted-ending romance (and told us, during its production, that the Margiela outfit here was his “favorite outfit ever”). And in time to admire it at the U.S. Open next week, we extol Nadal’s contribution to the long history of tennis fashion.

Is menswear pushing any edges this season? More like holding position. But in times of turmoil, a little stability isn’t such a bad thing.

Related:

• Archive: “Features”
• Articles by Harriet Mays Powell
• Table of Contents: Aug 25, 2008 issue of New York | Subscribe!