Among women of a certain age you can tell a lot about a person based on whether they identify more with Jen Lindley or Joey Potter. (If you have no idea who I'm talking about, you don't watch nearly enough reruns on TBS.) As Jen, Academy Award-nominated actress Michelle Williams played a bad ass girl from the city who'd been shipped off to live with her grandparents—but under her tough as nails exterior, her charming character had a heart of gold. And she was just plain more interesting. Which is why she originally won Dawson's heart and my vote for the coolest girl on "The Creek."

When menswear designer Scott Sternberg of Band of Outsiders explains why he chose Williams to star in his Fall 2008 campaign for Boy, his preppy off-shoot line of basics for the ladies, it sounds like he's reading from a similar script: "Michelle is beautiful, cool, low maintenance, funny, sweet, talented, smart and curious. And fun to hang out with. Therein lie the qualifications for shooting a Band of Outsiders look book."

And as evidenced by these pictures, boy does she ever know how to work a polished, tailored aesthetic. The decidedly feminine Williams (who allegedly went without the aid hair and make-up peeps) subversively sparkles in these androgynous autumnal pieces in a way that makes you want to slip into them all—especially a pair of the Band of Outsiders for Manolo Blahnik Canvas Spectators. Think Jen Lindley does Harvard...after watching "The Royal Tenenbaums" up in Dawson's bedroom, natch.

Boy is available at Barneys New York, 25 East Oak Street, (312) 587-1700.

- Caroline Stanley

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Similar Topics:fall 2008, look book love

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