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These Are 28 Of The Most Iconic Looks From "Insecure"

I'm not giving up hope for a spinoff, but for now I'll just imagine I have Molly's closet.

Amanda Davis
by Amanda Davis

BuzzFeed Staff

The tears still haven't dried since we watched the final episode of the final (🥲) season of Insecure. But one thing we'll always have are the 'FITS and style inspo that Issa, Molly, and the crew gave us for five seasons.

HBO / Giphy

So to celebrate this iconic show, I've put together a list of some of the best outfits worn — from Season 1 all the way to Season 5. Let's get to it!

1. Issa's black cutout dress with white trim (Season 2, Episode 1):

Issa in her home holding sangria
Insecure / HBO

This was Issa's (played by Issa Rae) post-breakup show-your-ex-what-he's-missing dress. It may have not worked for her back then, but this outfit still lives in my head rent-free.

2. Issa's Coachella crop top–and–skirt set (Season 3, Episode 5):

Molly and Issa at Coachella
Insecure / HBO

Honestly, everyone's Coachella outfit was great, but the floral skirt with the rust square-neck top is a favorite for sure. 

3. Molly's leopard-print swimsuit (Season 4, Episode 7):

Molly and Andrew in a pool
Insecure / HBO

This chic, deep-V one-piece is actually by Saint Laurent, not that we'd expect anything less from our girl Molly (played by Yvonne Orji). Also — just assume anything she wore on this vacation with Andrew belongs on the list. 

PS: It's on sale and still available in a couple of sizes, if you want to splurge ($386).

4. Kelly's pregnancy announcement dress (Season 5, Episode 10):

Kelly and her boyfriend standing in a resturant
HBO / Raymond Liu

The vibrant color, the wide sleeves, the feathers — yes to it all!

5. Basically, any time Issa wore her cream Telfar bag in seasons 4 and 5:

three images, each of issa wearing a small cream bag with different outfits
Insecure / HBO

Each outfit is styled PERFECTLY (somehow, even an old college sweatshirt looks chic), and the small Telfar is the cherry on top. 

6. Molly's asymmetrical peplum top (Season 3, Episode 6):

Issa and Molly laughing outside
Insecure / HBO

The pink top is by Oscar de La Renta, and I've never seen anything more "Molly." 

7. Just any of Tiffany's pregnancy outfits in Season 3:

Insecure / HBO

The patterns, the over-the-top heels, the dramatic dresses, and the pregnant glow. She killed it! 

8. Issa's cropped hockey sweater (Season 3, Episode 5):

Issa standing in confusion
Insecure / HBO

It's chill and casual, and it looks really, really comfortable to wear. And that lace-up detail takes it up a notch.

9. Kelly's, Molly's, and Issa's goodbye-party outfits (Season 5, Episode 9):

A crowd of people dressed up and sitting and standing outside
HBO / Merie Wallace

Kelly's (played by Natasha Rothwell) bustier and red satin suit may be her best outfit of the entire five seasons, Issa's tangerine minidress is adorable, and I need Molly's black-and-white halter dress in my closet ASAP.

10. Tiffany's pink-and-green Gucci dress (Season 5, Episode 1):

Tiffany holding Kelly's arm while they both hold drinks
HBO / Raymond Liu

This outfit may have been a controversy in the real world, but you've got to admit that it was a ~lewk~ in Insecure world. During Stanford's reunion, Tiffany (played by Amanda Seales) paid tribute to her sorority, Alpha Kappa Alpha, by wearing pink and green all weekend.

11. Molly's bold-colored power suits in seasons 1–5:

three images of molly in a magenta, teal, and maroon suit
Insecure / HBO

Yep, all of them!

12. Issa's "The Last Poets" jumper (Season 2, Episode 2):

Molly, Issa, Tiffany, and Kelly standing and talking at an event
Insecure / HBO

Fun fact: The Last Poets are a legendary group of poets and jazz musicians based in Harlem. They came together in the 1960s during the civil rights movement.

13. Issa's mint pant–and–cropped blazer set (Season 5, Episode 8):

Tyra Banks and Issa at an outdoor city ceremony
HBO / Merie Wallace

This was Issa's getting-the-key-to-the-city outfit, and it was perfect for the occasion...even if it was a dream.

14. Molly's Meshki Yasmin–style bustier and side-slit jeans (Season 4, Episode 1):

Insecure / HBO

Yes, this was a date outfit, and yes, Molly rocked it.

15. Issa's sparkly green dress (Season 1, Episode 1):

HBO / Giphy

One of the first outfits that introduced us to Issa's mirror reflection.

16. Lawrence's houndstooth jacket and Issa's cutout blazer (Season 4, Episode 8):

Lawrence and Issa walking through a room with handmade clouds
HBO / Merie Wallace

Whether I'm #TeamLawrence or not (I won't get into it), this coat is impeccably stylish. On top of that, Issa's power-red blazer is gorg!

17. Molly's asymmetric blazer top (Season 4, Episode 3):

Insecure / HBO

And speaking of open-shoulder blazers...they were obviously a big trend on Insecure, and I absolutely love it. You don't need warm jackets in Los Angeles, trust me.

18. Molly's Adidas set (Season 5, Episode 5):

Nathan and Issa sitting on a bench with Molly's dog
HBO / Glen Wilson

Yes, Molly's. 

This set is iconic for sentimental reasons. We know Issa grabs it from Molly's closet after visiting the hospital, but we actually see Molly wear this same set in Season 3! 

19. Issa's printed blazer and yellow ringer T-shirt (Season 3, Episode 4):

Issa standing outside of the We Got Y'all building
Insecure / HBO

Another sentimental add, but this is the outfit Issa wore when quitting We Got Y'all. It's like the gateway outfit for everything to come 🥺 .

20. Molly's denim on denim and Issa's plaid mesh turtleneck (Season 4, Episode 9):

Molly and Issa walking down the street
Insecure / HBO

We all know Molly is a fashion icon, but I can't help but love when she takes the most casual items (like denim shorts) and makes them something worthy of being pinned on my Pinterest board. 

And I love Issa and her love of plaid — it never fails!

21. Kelly's satin blazer-and-pant set with mini yellow bag (Season 4, Episode 5):

Kelly in a blue suit and white shirt
HBO / Merie Wallace

Kelly in a satin set has made the list twice, but she just looks too good to ignore. And that yellow bag? *Chef's kiss*

22. Issa's Biggie sweatshirt (Season 3, Episode 2):

issa eating lunch outdoors
Insecure / HBO

This sweatshirt actually came from small biz Lyftstyle Clothing. While this particular style is no longer in stock, they've got a ton just like it. 

23. Issa's striped romper (Season 3, Episode 8):

Molly and Issa smiling outside surrounded by other people
Insecure/HBO

And the hair crown is the perfect accessory, might I add. 

24. Molly's Alaïa fringe minidress (Season 5, Episode 10):

Molly is overjoyed
Insecure / HBO

Now, this is a dress someone wears on their birthday when they've made partner at their law firm, are in love, and have their family and best friends by their side. I LOVE this for her!

25. Issa's hole-y trench coat (Season 5, Episode 8):

Insecure / HBO

There's one more "What if it happened this way?"–scenario outfit on this list, but it's so worth it. Even if real-life Issa didn't get to wear it!

26. Tiffany's, Issa's, Kelly's, and Molly's Halloween costumes (Season 4, Episode 2):

the four women posing in Cleopatra, jigaboo, Nisi, and Clover Cheerleader costumes
Insecure/HBO

Seeing Kelly dressed up as Nisi from B.A.P.S. honestly just brings me joy.

27. The red bridesmaid dresses (Season 5, Episode 10):

28. Molly's Oscar de la Renta wedding gown (Season 5, Episode 10):

Molly and husband getting married
HBO / Raymond Liu

If this list were ranking starting with the best, just know this gorgeous gown would be No. 1. Did anyone else cry during this entire scene!?

Me seeing the evolution of fashion as the characters become more sure of themselves:

HBO / Giphy

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