2000s Dress To Impress Party Theme: What To Wear ASAP! 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. 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. Dress Like It's 2001 Salt Lake Magazine