Jessica Alba Just Reminded Us About This Inescapable Denim Trend From the 2000s Y2K Comeback The Ultimate Guide to Dressing Like the Early 2000s Icons YouTube Remember Wearing Dresses Over Jeans? It Was More Feminist Than You Realized HuffPost Life 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. Dresses Over Pants: The Quirky Y2K Trend Is Back In the early 2000's Apparently, I loved to wear dresses w jeans @ Los Angeles, California