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She’s seen in a hoodie with an iconic photo of Harriet Tubman on it — an homage to Tubman finally being chosen as the new face of the bill.Issa also mocks Trump’s MAGA campaign slogan, wearing a T-shirt James bought from Amoeba Music (a famed California record store she imagines Issa would shop at) that says “HUMP MAKE AMERICA GYRATE AGAIN.” “These are pieces she would’ve collected over the years.There’s a certain glow about Issa, Lawrence, and Molly and it’s not just all that melanin popping through your TV screens.They’re living good (enough) and looking even better for it, starting with a style overhaul.It also doesn’t help that Issa steps out of her comfort zone and into a pair of Gucci espadrille wedges (5) that she can’t walk in but insists on trying to make look sexy regardless.Issa thinks she’s being cute and unconventional, until she spots another woman in the bar wearing the exact same dress, with better shoes.The dress is a runway piece from Kenzo that James had to hire a seamstress to duplicate because another was never produced.
Immediately after accidentally getting his paycheck, she ditches her light and approachable pantsuits for darker “I mean business” colors, which continues throughout the season.“And when she doesn’t, it’s like, ‘Aw, you tried.’” Whatever look Issa goes for, James wants it to make a cultural statement: “I chose shirts, items, and graphics that could possibly generate more conversation and discussion.She wears everything from a real vintage Tupac and Biggie shirt to a sweater that says ‘The FBI Killed Fred Hampton.’ Anything that makes people go, ‘Wait a minute, where did she get that shirt from? That’s very specific to women of color our age.” For many of Issa’s looks, James says she’ll deliberately source from fresh black indie talent and give them the same boost that To pull off one of Issa’s most questionable looks this season, an unflattering, puffy, high-neck, denim-khaki dress she wears to go pick up men at a bar with Molly, James leaned all the way into Issa’s awkwardness.At work at her sometimes-racist nonprofit job We Got Y’all, that look won’t change. What he had obviously wasn’t working, so she’s gonna show him what he’s missing and scratch a couple more itches along the way,” James says, referencing Issa’s affair with an ex last season.But in her personal life, which now includes a lot of Tinder swiping and plotting to get Lawrence’s attention, she’s gone for a more grown ‘n’ sexy approach. “You’ll see a difference in her effort in what she wears.” In season one, Issa wears looser tomboy interpretations of femme clubwear, but by season two, with a subtle weight loss taking effect, she experiments with body-con dresses and crop tops, even when playing host at her casual house party (to not so slyly try to impress Lawrence).