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The Inspiration

Naomi's pair fit her, which is one of the most important qualifications for a nonsloppy look. One of the first things you'll notice when shopping today's luxe options is that they aren't sized just as a small or medium but in a waist measurement (in the same way your skinnies are). Rolling or cuffing them like you do your boyfriend jeans is also the easiest way to avoid an awkward interaction between pant leg and shoes. Naomi's simple Ancient Greek Sandals are one of Spring and Summer's trendiest shapes, but with a superflat base, they're less clunky than Birkenstocks. For the final outfit statement, she picked Oliver Peoples West sunglasses.

Image Source: Getty / Bauer-Griffin
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