This week we're kicking things off with Holly Golightly from Breakfast at Tiffany's, because if anyone knew how to shop, it was the original New York It Girl. She's classy, carefree, and seriously chic, whether she's in her Uptown best munching on a croissant outside those glistening Fifth Avenue windows or chilling Downtown singing with her guitar. Below, we've rounded up the 50 best items for that friend who's a wannabe Audrey Hepburn (you know who we're talking about!). Click through for '60s-inspired dresses, ladylike staples, and yes, even a special something from Tiffany's. Because it wouldn't be the perfect gift for a modern-day Holly without that little blue box.
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