This white slip dress debuted on the Resort 1990 runway, worn sans jacket by British model Gail Elliott, one of Michael’s runway favorites. The simple silhouette is encrusted with hand-embroidered crystals to create a luminous, textural effect. For the anniversary collection, the dress was styled on model Bella Hadid with a sleek, tailored tuxedo jacket draped over her shoulders. This sought-after slip dress was featured on countless magazine covers throughout the 1990 holiday season and stole the spotlight in a legendary portrait of Madonna as Glamour magazine’s Woman of the Year. (A photograph that Michael now owns and passes in his hallway every day.)