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. Gen Z is bringing back dress over jeans fashion trend and millennials are reeling Remember Wearing Dresses Over Jeans? It Was More Feminist Than You Realized HuffPost Life In the early 2000's Apparently, I loved to wear dresses w jeans @ Los Angeles, California