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. Remember Wearing Dresses Over Jeans? It Was More Feminist Than You Realized HuffPost Life Buffalo David Bitton Jeans 2000s Print Advertisement Ad 2006 Sexy Long Legs eBay 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.