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.

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  • Julie

    OMG I saw Issa speak at a conference this past weekend and she looked SO GOOD. Like, even the way she was walking – I just stared, mouth gaping, probably drooling. Perfect mini-dress, effortless jean jacket. Also, Yvonne was on the side of the stage wearing an oversized camo jacket over a cold-shouldered pink mini. You’re welcome for this very important intel.

  • rolaroid

    FINALLY something, ANYTHING, about Insecure!!

  • rolaroid

    What about all her super rad and political t-shirts! The Last Poets, FBI KILLED FRED HAMPTON, All her hip-hop tees. Don’t whitewash over that!

    • Alexia

      The last poets tee is shown…

      • rolaroid

        I know, but it’s not mentioned, the focus is on the pants.

    • Shegirl

      I googled Fred Hampton! She’s puttin us on to political shit!!!

    • prairie dogs

      I looove and need the fred hampton sweatshirt. All her political shirts are so good. I also loved Molly’s Trayvon hoodie in the finale.

      • rolaroid

        Loved it too! Took a minute to see it because her hair was hiding it and I wondered, “Is that a statement hoodie or just some brand hoodie.” Want the Fred Hampton tee as well. He is such an important figure, not enough notoriety.

    • Alison

      White wash big time. After ignoring Insecure all summer this is what we get? How on earth is it possible to write an article about Insecure with zero mention of blackness? At. All. With everything you could possibly say about the meaning of the fashion on this show, we’re talking about the weather in LA and the fact that her character wears no pants in the house? Reading this, I got the impression that the writer just took screen shots of cute outfits with the show on mute and Taylor Swift on repeat in the background. Hella lazy and hella disappointing.

      • rolaroid

        I know!! I was like, def showing how white you are by ignoring all this. The interview with Ayanna James that is linked to even says “I can use that platform to educate” and I’m surprised that was ignored. Apparently it’s not working…

      • I feel you, but I will say, shes writing about the clothes the way that she can relate to them. She can’t relate to the blackness part, she can’t relate to the racial and politcal statements the shows fashion makes. Which is why WOC will read it and find it lacking but in the grand scheme of things, I think its a good article. She did what she could, with what she could see and and understand. The real answer is to get a WOC writer on staff or a freelancer they can go to. Diversity isn’t just about the stock photos on your site or the topics you choose to write about but the diversity in views that you present to the readers. This is a show about black women, black women should be able to relate to the article a black womans voice should be heard about this topic and what it means. MR does try, so we can atleast give them that.

        • Alison

          I agree with you all the way Karolena. MR does try and that’s exactly why I was so disappointed with this write up. It shows apathy and lack of trying. “Ribbon straps” is the caption for one of the photos. That’s not even a full sentence! If the writer can’t relate to the blackness, is barley skimming the surface on the fashion, and seems like they haven’t watched the show, why is she writing this article? And why publish it? Also, I am not usually one to comment, but this is the second time in recent weeks that I read an article on MR, and was like “Hey! They missed the black part!” An article about yellow taking over millennial pink with no mention of Beyonce’s yellow dress in Lemonade? What?!

          • lol “Ribbon straps” I know what you mean, I think she probably watches the show and I think she probably felt the need to write this because she relates to the characters. The parts that she can’t relate to she didnt want to discuss in the article. Which is why a WOC writer should have been called in. This was them trying, it just wasnt that great. I know what you mean, that Dress like Rihanna article……. what about the black part? And if MR is wondering why the black part has to be included, it’s becasue we are black and our experiences and viewpoints are rarely shraed but are still so important. The whole existence of Insecure is proof of that. We need shows like insecure for us but also so girls like the writer can see our truth. Just like we need WOC writing about it, so the rest of the world can see our truth.

          • Haley Nahman

            Hearing you hearing you hearing you.

          • Haley Nahman

            And I’m sorry for not doing better on this one.

          • prairie dogs

            Really well put (the yellow article was especially head-scratching). I wish MR had more women of color as staff writers. 🙁

          • prairie dogs

            To clarify– I mean that a more diverse set of writers would help enrich and expand the perspectives for the whole site/office. Not that only women of color writers should be addressing topics like Beyonce (single-handedly!) introducing Oshun-style saffron yellow as the new millennial pink.

        • I completely agree.

  • Ally H

    OMFG I have been waiting for this article

  • sugar_magn0lia

    Totally missing her political and pop culture statements via clothing.

    • Thamsa

      Which I think is the best part !!

  • KellyMarie_Calamari

    Why in the world wouldn’t I want to look like a character in That 70’s Show?

  • bb222

    Agree that the outfits are amazing but… sometimes i think there is a bit of a mismatch with the character and her life story. Most obviously, her finances don’t match these clothes. But also, they are so perfect… shouldn’t some of her clothes be awkward like she is (the scene with the mini dress does achieve this wonderfully)? Like is it supposed to be a part of her character that she is SO DAMN GOOD at putting an outfit together? Is Issa cutting up her tshirts on the weekend? Am I just hoping for even more from such a good show…. maybe.

    • Ginger

      I saw an interview with Ayanna james that said Issa’s outfits are meant to be a bit awkward. That’s why she never looks “perfect” like Molly does. And why she might mix converse with a mini dress or whatever. But yeah — it works so well!!

  • Ginger

    It CANNOT be ignored that the pink mock turtleneck features the ICONIC image of Cam’ron in a pink fur hoodie on a flip phone. I DIED:

    • If anybody knows where that Cam’ron mock neck came from please post it in here!

    • Haley Nahman


  • Selena Delgado

    That mini-dress was killah!!! It distracted me from the scene because it was so dope. She had Gucci platforms in that scene too. Love her

  • spicyearlgrey

    god i luv everything about this show

  • YAAAAAS I just discovered this show a week ago and devoured two seasons in a few days.

    Aside from the rad outfits that Issa has, the soundtrack is A+ and the boiz are v v cute.

    • Aaaand that looks outfit with raw striped satin blouse and hoop earrings and cropped fringe flares is a goddamn delight.

  • Kelsey Moody

    Up next, Molly’s lawyering work outfits plzzz!!!?

  • I adored the styling in Insecure, so sad the season’s over!

  • I was hoping this article would discuss the many political statements made through her outfit choices. 🙁

    • Haley Nahman

      You’re right, I should have mentioned. In quickly skipping through in search of full looks I missed a lot of the nuanced messaging. I’m sorry 🙁

  • kionah

    Honestly, this is a poor excuse for a style guide. Totally missed the opportunity to reflect on the political statements and didn’t even bother to find actual clothes worn in the show (lots of black owned businesses). I found a good one here

    • Haley Nahman

      You’re right, I rushed this and didn’t do it justice, thank you for linking to this!

  • cemberli

    The pink turtle neck is also the Cam’ron meme and that is important

  • let us not forget that the pink turtle neck is also the cam’ron meme!!!