Over the weekend, the 19-year-old Harvard student stepped out wearing a breezy Urban Outfitters dress. Nope, she wasn't vacationing in sunny Miami. She actually was spotted on the chilly New York City streets.
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So how'd she make the summery piece work in the winter? A few layering essentials helped her get the job done. First, tights are a must. A sheer pair—like Obama's—will allow your legs to show through while protecting your gams from the bone-chilling wind. Layering a trendy puffer coat also helps. The bigger the better, so don't be afraid to go up a size or two. And no need for heels. Throw on a pair of combat boots—like celebrity-approved Dr. Martens ($135; nordstrom.com)—with rolled down tube socks, and you'll be good to go.