How Guys Used to Dress in 90s TikTok 6 ways to style dress over jeans as the controversial Y2K trend makes a comeback for autumn To all of the Gen X women, what was the best 90s fashion for you guys? (Also, happy Women's History Month!) : r GenXWomen 90s Outfits for Guys Trendy, Party, Cool, Casual Gen Z is bringing back dress over jeans fashion trend and millennials are reeling 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.