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. Dress Over Jeans Trend From the 2000s PS Fashion Dresses Over Pants: The Quirky Y2K Trend Is Back Remember Wearing Dresses Over Jeans? It Was More Feminist Than You Realized HuffPost Life