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. 15 Celebs Wearing Low Rise Jeans During the Early 2000s Who What Wear 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. 6 ways to style dress over jeans as the controversial Y2K trend makes a comeback for autumn 15 Celebs Wearing Low Rise Jeans During the Early 2000s Who What Wear The 2000s dress over jeans trend was atrocious