Issa Rae has a lot to celebrate as the last season of Insecure [1] premieres [2] on HBO and her stylist, Aliétte's Jason Rembert [3], hooks her up with all the perfect party outfits to boot. After revealing just the right amount of underboob [4] 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 [5]. It's simple: just throw on a jean bralette over your oversize button-down shirt and complete with a pair of baggy slacks [6].
Issa smartly coordinated the look with white sneakers and chunky, gold hoop earrings from Sister Love [7], 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 [8], 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.
Prada Organic Denim Top
Prada Organic Denim Top [10] ($690)
Philosophy Di Lorenzo Serafini Cropped Denim Bralette
Philosophy Di Lorenzo Serafini Cropped Denim Bralette [11] ($249, originally $356)
Cider Floral Denim V-neck Tank Top
Cider Floral Denim V-neck Tank Top [12] ($14, originally $18)
Missguided Blue Co Ord Deconstructed Denim Bralette
Missguided Blue Co Ord Deconstructed Denim Bralette [13] ($17, originally $34)
REDValentino Patchwork Denim Top
REDValentino Patchwork Denim Top [14] ($395)
Fashion Nova Denim Party Halter Crop Top
Fashion Nova Denim Party Halter Crop Top [15] ($31, originally $45)
Tibi Summer Denim Strapless Bralette
Tibi Summer Denim Strapless Bralette [16] ($325)
AG Jeans Hebe Top in Vendetta
AG Jeans Hebe Top in Vendetta [17] ($126, originally $168)
Alessandra Rich Crystal-Embellished Denim Bustier
Alessandra Rich Crystal-Embellished Denim Bustier [18] ($715)
Urban Revivo Denim Bustiers With Strap
Urban Revivo Denim Bustiers With Strap [19] ($26)
GCDS Bling Denim Bra
GCDS Bling Denim Bra [20] ($603)
Shein Raw Hem Tube Denim Top
Shein Raw Hem Tube Denim Top [21] ($8, originally $15)