Dress Over Pants? Why not.. When discussing fashion trends of the by Starryli Medium 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 Y2K Pepe Jeans Midi Dress in Yellow Cotton Pop Sick Vintage Are You Ready for Dresses Over Jeans Again? The New York Times 2000s Fashion History: Why did we layer jeans under dresses and skirts? : r femalefashionadvice