Dresses with Jeans: A Controversial Fashion Trend from the 2000s POV: Its the #2000s & the cool girls are wearing jeans under dresses. #nostalgia #2000sfashion Vintage Y2K Pepe Jeans Midi Dress in Yellow Cotton Pop Sick Vintage 2000s Fashion Is Making A Comeback It Must Be Stopped Denim Milkmaid Dress (M L L) Retro and Groovy 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.