The Insecure star hosted the CFDA Fashion Awards at the Brooklyn Museum in New York City on Monday, and during her monologue, she mocked the 40-year-old rapper -- right in front of his wife, Kim Kardashian West, who received the fashion council's first-ever Influencer Award.
"I'm about as fashionable as Kanye is black," she said during the ceremony, according to USA Today. "Only when it's convenient. That joke was my choice, just like slavery."
The Los Angeles native was referencing the comments Kanye made during his interview with TMZ last month, where he implied that slavery was "a choice" for African-Americans.
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"You hear about slavery for 400 years. For 400 years?! That sounds like a choice," he said at the time. "You were there for 400 years and it was all of y'all? It’s like we're meant to be in prison. I like the word 'prison' because slavery goes too direct to the idea of blacks… prison is something that unites us as one race."
West later clarified his remarks via Twitter, writing, "To make myself clear. Of course I know that slaves did not get shackled and put on a boat by free will. My point is for us to have stayed in that position even though the numbers were on our side means that we were mentally enslaved."
"The reason why I brought up the 400 years point is because we can't be mentally imprisoned for another 400 years," he continued in a series of tweets. "We need free thought now. Even the statement was an example of free thought It was just an idea. Once again I am being attacked for presenting new ideas."
Issa also made a bold statement earlier in the night, walking the red carpet in a custom off-the-shoulder ensemble created by Pyer Moss that featured a controversial belt. The accessory was emblazoned with the words, "Every N**** Is a Star," lyrics from Boris Gardiner that were a part of the Oscar-winning Moonlight soundtrack.
While Issa later roasted Kanye, she had nothing but great things to say about Kim while chatting with ET ahead of the awards show.
"I mean, there's no doubt that Kim K has influenced an entire fashion industry, an entire generation of women," she told ET's Nischelle Turner on the red carpet. "And [Icon Award recipient] Naomi Campbell is a legend in her own right. You know, to grow up and see her as a young, dark skin girl. To see her on runways, to her killing it in spreads... she made me feel like, 'Wow, maybe I could.'"
"Everyone looks amazing," she added. "It's an honor to be here."
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In addition to being one of the standout stars at the CFDA Fashion Awards, Issa is also turning heads in the July issue of Cosmopolitan, where she opens up about why appearances are so personal.
"I'm going to look how I want to look -- it's going to be on my own terms," she explains. "If people criticize my look, it really does not matter to me. It's about how I feel."
"Confidence comes from knowing your s**t is good," she continues. "I'm for sure confident when it comes to work and trying to fulfill my dreams. Socially, the confidence has teetered, but that's growing as I'm coming into who I am."