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. Jessica Alba Just Reminded Us About This Inescapable Denim Trend From the 2000s In the early 2000's Apparently, I loved to wear dresses w jeans @ Los Angeles, California Dresses Over Pants: The Quirky Y2K Trend Is Back