Y2K Fashion 101: How the Millennium Started Trending All Over Again Vogue 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. 25 Early 2000s Fashion Trends That Feel Wonderfully Chaotic Today 2000s Fashion Is Back, and It Looks Way Better Than You Remember GQ