Look of the Day

Jeffrey Ufberg/WireImage

October 4, 2009

1. Olivia Wilde

WHAT SHE WORE A seamed gray Helmut Lang sheath with a little leather jacket and Brian Atwood patent pumps

WHERE Outside the Late Show with David Letterman studios

WHY WE LOVE IT Wilde toughened up her ladylike dress with the perfect fall topper-a versatile cropped leather jacket. Toss one on over a classic daytime sheath for an edgy post-work look.
Jack/FilmMagic

October 4, 2009

2. Claudia Schiffer

WHAT SHE WORE Schiffer paired a vintage-inspired sweater and tweed jacket with wide-leg MiH jeans

WHERE Running errands in London
Tom Meinelt/SplashNewsOnline.com

October 4, 2009

3. Maggie Gyllenhaal

WHAT SHE WORE Gyllenhaal dressed for fall in a patterned dress, rustic sweater, plaid scarf and black leather boots

WHERE Walking in New York City
Justin Campbell/FilmMagic

October 4, 2009

4. Michelle Trachtenberg

WHAT SHE WORE Trachtenberg accessorized her jeans and peacoat with a floral scarf and zipper-bedecked boots and a black and blue bag, both from Botkier

WHERE Leaving the Gossip Girl set in N.Y.C.
Jack/FilmMagic

October 4, 2009

5. Elle Macpherson

WHAT SHE WORE Macpherson topped off her print dress with a fur-trimmed vest and added knee-high boots and oversize sunglasses

WHERE Out and about in London

Olivia Wilde in Helmut Lang and Brian Atwood — Jeffrey Ufberg/WireImage

October 4, 2009

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Olivia Wilde

WHAT SHE WORE A seamed gray Helmut Lang sheath with a little leather jacket and Brian Atwood patent pumps

WHERE Outside the Late Show with David Letterman studios

WHY WE LOVE IT Wilde toughened up her ladylike dress with the perfect fall topper-a versatile cropped leather jacket. Toss one on over a classic daytime sheath for an edgy post-work look.