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Issa Rae has a lot to celebrate as the last season of Insecure premieres on HBO and her stylist, Aliétte’s Jason Rembert, hooks her up with all the perfect party outfits to boot. After revealing just the right amount of underboob in London-based brand Rokh, Rae swapped a fancy cocktail dress for denim separates by Miu Miu at the Insecure Fest on Oct. 23 in LA. The decidedly casual turn provided all the outfit inspiration we need for fall. It’s simple: just throw on a jean bralette over your oversize button-down shirt and complete with a pair of baggy slacks.
Issa smartly coordinated the look with white sneakers and chunky, gold hoop earrings from Sister Love, a jewelry collaboration between Simone I. Smith and Mary J. Blige. She tied a white shoelace through her belt loops, just to bring the whole outfit even more of a cool factor, and wore a long braided hairstyle. As she was photographed hanging out with her castmates, we saw every reason to round up similar cropped pieces that would do the trick — one of which is by Prada, Miu Miu’s “older sister” brand. Read through all the options after the jump to round out your seasonal wardrobe just like Issa’s.