Dress Over Pants? Why not.. When discussing fashion trends of the by Starryli Medium 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 Fashion History: Why did we layer jeans under dresses and skirts? : r femalefashionadvice Vintage 2000s Y2K Cop Copine Subversive Prairie Milkmaid Style V Neck Thee Cultivator Dresses Over Jeans: A Retrospective : r Fauxmoi