Vintage 2000s Y2K Cop Copine Subversive Prairie Milkmaid Style V Neck Thee Cultivator 15 Celebs Wearing Low Rise Jeans During the Early 2000s Who What Wear 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