Dress Over Pants: Is There A Stylish Way Of Wearing It Sans The Y2K Nostalgia? Y2K Fashion is Problematic. Here's Why Art & Object 15 Celebs Wearing Low Rise Jeans During the Early 2000s Who What Wear The Worst Early 2000s Fashion and Outfits Celebrity Outfits From Early 2000s 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.