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We’re used to seeing Brooke Shields dazzle in smartly tailored red carpet gowns, but last night in New York City it was an very different look that caught our eye. For the release of blues-rock songstress Jill Hennessy’s (below, left) new album, I Do, the former Calvin Klein campaign star stepped out in a rock star-inspired look that paired a distressed leather jacket with a plain tee and black jeans tucked into sleek leather boots.

The model wasn’t the only star to take a downtown approach at the Cinema Society-hosted celebration. Hennessy herself slipped into a sleeveless, multi-patterned metallic dress complemented by a triple-strap metal cuff and loose, relaxed strands. Meanwhile, actress Patricia Clarkson (below, center) took a page from Shields and opted for black leather, although her lady-like platform shoes and bow-adorned red handbag gave her a more conservative edge.

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Designer Nicole Miller (above, right) was also on hand in an embellished all-black ensemble. And even in their casual frocks, star couple Alec and Hilaria Baldwin (below) stole the spotlight in matching, autumn-appropriate ensembles.

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Inside the venue, other late-night revelers like Orange Is the New Black star Lea DeLaria, Bobby Flay, and Dylan Walsh lent their ears as Hennessy picked up her guitar and began belting out her favorite hits.