The Y2K Dress Over Pants Trend Is Backand More Elevated Than Ever Vogue Denim Milkmaid Dress (M L L) Retro and Groovy 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 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. Dresses Over Pants: The Quirky Y2K Trend Is Back