With the kind of effortless off-duty style that first makes you think, "She's pregnant?!" and then, "I want what she's wearing," Victoria's Secret model Alessandra Ambrosio caught our attention making her way around NYC. It's a perfect play on easy pieces and relaxed silhouettes, but the result is far from sloppy. Instead, luxe additions like a covetable Céline tote and a pair of classic riding boots lend polish to a slouchy Joie sweater and dressed-down leggings. A pair of Chanel shades and an essential cool-girl layer — the leather jacket — finish the look. Love the casual-cool vibe? Shop our editors' picks to channel Alessandra's dressed-down edge.