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 Over Pants? Why not.. When discussing fashion trends of the by Starryli Medium Embrace Y2K Fashion: Mini Dress Over Jeans Style 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. Dresses Over Pants: The Quirky Y2K Trend Is Back The 11 Most Tragic Things We Wore In The Early 2000s Will Make Us Cringe Now PHOTOS