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 Jessica Alba Just Reminded Us About This Inescapable Denim Trend From the 2000s Ashley Tisdale's 2000s Outfits 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. Moschino Jeans 2000s Vintage Denim Western Dress AMO Vintage