Vintage 2000s Y2K Cop Copine Subversive Prairie Milkmaid Style V Neck Thee Cultivator Dress Over Pants? Why not.. When discussing fashion trends of the by Starryli Medium Dress Over Pants? Why not.. When discussing fashion trends of the by Starryli Medium Remember Wearing Dresses Over Jeans? It Was More Feminist Than You Realized HuffPost Life Moschino Jeans 2000s Vintage Denim Western Dress AMO Vintage 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.