Photo: Devon Jarvis/Studio D

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Designer Collaboration: Milly and Sperry Top-Siders
Nothing is more comfortable than Sperry shoes—I wear them all summer long. With Milly's ladylike, vintage-inspired prints, you get the perfect combo of preppy and pretty.

Wedge, $195, and rose-print boat shoe, $125; SperryTopSider.com.
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