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. 2000s Fashion History: Why did we layer jeans under dresses and skirts? : r femalefashionadvice Ashley Tisdale's 2000s Outfits Gen Z is bringing back dress over jeans fashion trend and millennials are reeling