Nineties Milk The dress over jeans look emerged in the early 2000s (c. 20022005), during a period defined by maximalism and experimental layering. This Instagram The early #2000s trend of wearing dresses over jeans was a popular #y2k era look, often featuring a long dress, like a babydoll or slip dress, layered over flared or skinny jeans. The 2000s Fashion Trends That Defined the Y2K Aesthetic Who What Wear 2000s Dresses Over Jeans