How did you dress in the early 2000s? : r Millennials 2000s Dress To Impress Party Theme: What To Wear ASAP! Clothing styles from the early 2000s JEAN WEEK!! And then also one non denim outfit cause I can't help myself but dress like an early 2000s gay aunt : r oldhagfashion The 2000s Bandage Dress Is Back, Thanks To Gen Z 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.