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When she carried a wine glass like a clutch, well, we tried

A sheath or architectural silhouette works well, but avoid anything flirty or joyful, such as an A-line or fit-and-flare." She recommends scanning Farfetch and Net-a-Porter for higher-end labels like Alexander McQueen, Rick Owens, and Ann Demeulemeester, or shopping COS, Banana Republic, and Zara for lower price points