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 6 ways to style dress over jeans as the controversial Y2K trend makes a comeback for autumn Ashley Tisdale's 2000s Outfits 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.