Dress on Jeans Y2k 21 Reminders Of How We Used To Dress In The '00s 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. 6 ways to style dress over jeans as the controversial Y2K trend makes a comeback for autumn Blue denim mini dress with button up front and short Depop