In its 1999 summer issue, smart magazine featured a special titled “Battle of 1,000 Stylish Men,” showcasing street snaps of fashion-forward individuals from 14 cities including Tokyo and Osaka.
At the time, Japan’s men’s fashion scene was a vivid crossroads where streetwear, hip-hop, American casual, and visual kei rock styles coexisted and were being actively reinterpreted. It marked both the culmination of 1990s culture and the beginning of a stylistic shift that would define the early 2000s.
Tokyo-born streetwear brands that had been gaining traction since the mid-90s were finally stepping into the mainstream, and the rise of hip-hop culture brought a surge in stylistic influence from Japan’s growing hip-hop scene.
Oversized silhouettes and American-inspired hip-hop looks dominated the streets—often paired with gender-fluid makeup, metallic accessories, and iconic pieces from Levi’s, Nike, Red Wing, and Ralph Lauren. Though American casual was at its peak, there was a clear thirst for something new.
That fragmented and hybrid era would soon be disrupted by the sharp, minimalist elegance of Hedi Slimane’s Dior Homme, signaling a dramatic shift in the way masculinity and fashion were expressed in Japan throughout the 2000s.
