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"I never thought of khakis for evening," says 44-year-old children's clothing designer Iben Dismond, who wears the cheapest jeans she can find to her kids' playground by day and upgrades to fitted, cropped denim and heels at night. Here, she goes for a pair of rolled-up boyfriend khakis (Banana Republic, $70) with a sequined top (Gryphon New York, $365) and gladiator sandals (Giuseppe Zanotti Design). "This is how to do khaki—turn it into something special," says Iben.
Hoops and cuff, Robert Lee Morris. Ring, Ben-Amun by Isaac Manevitz. Clutch, VBH.