Dresses with Jeans: A Controversial Fashion Trend from the 2000s How did you dress in the early 2000s? : r Millennials 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. An ode to the romanticism of late 90's early 2000's gowns, part 1 : r whatthefrockk Most Controversial Dresses Of The 2000s