All of Issa Rae’s Best Outfits on ‘Insecure’

Wardrobe can make, shape, break characters; the believability of a cast can live or die by how its dressed. Insecure costume designer Ayanna James seems to understand her power implicitly. The clothes on the show are so much more than the sum of their parts. They’re thoughtful but not overwrought, accessible but not plain, surprising but not distracting. They’re also very L.A. which, to me, is refreshing.

“I feel like every character on the show is relatable,” James told the LA Times. “You either know someone like that or you’ve been that person at a period in your life… I know that costumes on television are prime real estate. I can use that platform to educate … to promote … to influence how the viewer feels.”

If creator and writer Issa Rae is the only person who could possibly play the lead of the same name, James is surely the only one who could dress her. The collaboration between them mirrors the tone of the show: casual magic. And on Season 2, which just wrapped last night, the two of them had me screen-shotting non-stop. Please validate my efforts by reviewing all of Issa’s best looks this season, presented below, sans spoilers.

Let’s go.

Insecure’s L.A. is always a breezy 72 that cools to 68 in the evening. It’s the kind of weather that enables summer mermaids and fall freaks to coexist without outfit-shaming each other because everyone wears what they want. Issa, for instance, is jacketed often:

That’s a D.A.R.E. shirt, FYI.

ATTN all: camo.

This black-and-white treasure single-handedly changed my mind regarding cropped denim jackets. Also, this ripped and knotted T-shirt is not the first time I’ve considered taking scissors to a shirt because of this show.

Exhibit A.

and Exhibit B.

Bye Daniel.

This shirt is embroidered, if you can’t tell, and with its dangling bottom hem, it’s what I call a non-committal crop. Here she’s seen walking around her apartment complex, which starts to feel like home the more you watch.

Mail time/calf decoration.

Speaking of pants, she basically never wears them at home, which is a delight.

I hope that’s a rash guard.

Trust me when I say she wasn’t wearing pants here, but more importantly: note the pink mock-turtleneck, perfect for stalking an ex-boyfriend.

Her going out looks are equally good:

Midriff is back.

This dress resembles a HoHo in a good way and I need it.

Ribbon straps.

This is a mini-dress. Sign me the FUCK up.

Above, how to wear wide-legged pants in orange suede and not look like a character from That ’70s Show.

Insecure is better than its clothes, but it’s better for them, too. Together they achieve the kind of symbiosis most TV stylists dream of, where the clothes both support and enhance the characters. No easy feat, considering the unmatched expressiveness of its star.

Want more Insecure? Listen to this episode of The Call featuring Yvonne Orji, who plays Molly on Insecure. Photo via HBO.

Haley Nahman

Haley Nahman

Haley Nahman is the Features Director at Man Repeller.

More from Archive