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. 15 Celebs Wearing Low Rise Jeans During the Early 2000s Who What Wear The 2000s dress over jeans trend was atrocious Remember Wearing Dresses Over Jeans? It Was More Feminist Than You Realized HuffPost Life