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A plaid shirt (Arnold Zimberg, $175) and slouchy pants (IRO, $158) have a soft, washed-out texture and slightly sun-bleached palette...as if you've been wearing them in for years. The pants won't look like pajama bottoms if you add substantial accessories: a necklace that whimsically combines chains and appliqués (Malandrino), a patchwork bag (Jamin Puech), and glamorous platform clogs (Chanel) that Lipton calls "insane!" (she has a thing for tall shoes). Tank, American Eagle Outfitters, $16.