Jessica Alba Just Reminded Us About This Inescapable Denim Trend From the 2000s 11 Stylish '90s Men Whose Iconic Looks You Should Steal For 2019 Will the 90s and 2000s hip hop style make a comeback? 90s Outfits for Guys Trendy, Party, Cool, Casual 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.