Lauren Hutton in Gryphon New York

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West by Southwest
This lived-in look is textbook Lauren Hutton—her clothes always seem like things she's owned and loved forever. The intentionally rumpled trenchcoat (Gryphon New York, $610) works nicely with slightly baggy, tattered "boyfriend" jeans (I Heart Ronson for JCPenney, $44). The mix of rancher casual and Native American craft is, of course, associated with two Laurens: Ralph L. did the plaid shirt (Ralph Lauren Blue Label, $165); the turquoise and silver necklace and bracelet (Vicki Turbeville) look like something Lauren H. might have picked up on her global travels—she collects accessories worldwide and is crazy about "things I bought when I was with good friends that have good stories surrounding them."