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. 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. How To Dress Like Gisele Bndchen In The 2000s This Winter British Vogue Quick Guide to 2000s Fashion Central Casting Dresses Over Pants: The Quirky Y2K Trend Is Back