The 2000s Dress Over Jeans Trend Is Back In Full Force Dress Over Pants? Why not.. When discussing fashion trends of the by Starryli Medium The Y2K Dress Over Pants Trend Is Backand More Elevated Than Ever Vogue Gen Z is bringing back dress over jeans fashion trend and millennials are reeling In the early 2000's Apparently, I loved to wear dresses w jeans @ Los Angeles, California 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.