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 did you dress in the early 2000s? : r Millennials Y2K Fashion: How To Dress Like You Just Stepped Out Of The Early 2000s TC Elli's 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. 39 unforgettable Y2K fashion trends from the 2000s that are making a comeback