5. Junya Watanabe
The protégé of Rei Kawakubo is one of the greatest designers of our time. After spending close to a decade studying under Kawakubo, Junya Watanabe started his eponymous label under the Comme des Garçons collective umbrella, and later headed the Junya Watanabe Comme des Garçons label. More so than any other brand, his clothes have explored the ways in which technology and style can complement one another, resulting in clothes that aesthetically are beyond what anyone else is doing for menswear at the moment while performing under any and all conditions.
Watanabe is celebrated for taking an individual garment that had seemingly been perfected, taking it apart, and re-constructing it in a way that no one could even conceive of. Kawakubo's mentorship does come through in his men's work at times, but Watanabe is never pursuing the avant-garde goal of trying something completely out of bounds. He claims that his men's clothes are just made to be worn and don't have any meaning or philosophy behind them, and that seems about right. With a lot of Junya Watanabe's clothing, we don't even know we want it until he creates it.