2000s Fashion History: Why did we layer jeans under dresses and skirts? : r femalefashionadvice 2000s style: how to rock the 2000s fashion trends Dresses Over Jeans: A Retrospective : r Fauxmoi Are You Ready for Dresses Over Jeans Again? The New York Times 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. Vintage 2000s Y2K Cop Copine Subversive Prairie Milkmaid Style V Neck Thee Cultivator