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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

Artists like Jay-Z, Missy Elliot, Lil Kim and Aaliyah were driving forces behind the merging of streetwear and high-end luxury, a staple of the Y2K aesthetic