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Hutton has a history with menswear, ranging from down-and-dirty denim to Giorgio Armani's slouchy '70s pantsuits, from Calvin Klein's minimalist '80s silhouettes to modern practitioners like Paul Smith (shirt, Paul Smith London, $295), Ralph Lauren (pants, Lauren by Ralph Lauren, $179), and the Olsen twins (blazer, The Row). Balanced proportions—here, the juxtaposition of a perfectly fitted jacket and easy bottoms—are crucial to pulling off anything oversize. Her shoes are Sperry Top-Siders, the boat shoes she made famous: "I like the way they feel. They make you prance rather than shuffle." Ring, Me & Ro.