As a fashion designer, he has had his critics. They say his clothes are too simple, that they don’t push the envelope. As New York’s fashion critic Cathy Horyn wrote of Yeezy Season 2: “This second round of drab, broken-down basics proved he can’t be taken seriously as a designer.” However, even though the fashion powers that be don’t see him as a legit contender — his impact on men’s fashion is undeniable.

That’s because, in many ways, he unknowingly sparked fashion’s obsession with ungendered, fluid clothing. Before Hood by Air or Jaden Smith, West was dressing with no one gender in mind, proudly pairing pieces that are typically feminine with pieces that are typically masculine. And in an industry like hip-hop, that has often butted up against any sort of feminine ideal, that matters. In embracing feminine fashion, West was breaking the hyper-masculine norm. As rapper Lord Jamar said of West in 2014: “This feminine, emasculated style that’s trying to infiltrate hip-hop, he’s one of the pioneers of that.” And Jamar, a noted homophobe, didn’t mean that as a compliment.

Despite the criticism thrown his way, West has also, throughout his career, been unafraid to take style chances, seeing if something like a fully bedazzled matching jacket could work with ripped jeans (it didn’t).

Here are three instances that West changed men’s fashion — and made it all the more interesting.

From the very beginning, Kanye West was unafraid to embrace pink

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Way before Jaden, West wore skirts.kanye2

West made skinny jeans fashionable — or at least he thinks so.

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