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. 2000s Dress To Impress Party Theme: What To Wear ASAP! Y2K Fashion: How To Dress Like You Just Stepped Out Of The Early 2000s TC Elli's How did you dress in the early 2000s? : r Millennials 47 Dress like 2000! ideas 2000s fashion, 2000s fashion outfits, early 2000s fashion 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.