These Are 28 Of The Most Iconic Looks From Insecure
The tears still haven't dried after watching the finale episode of the final (🥲) season of "Insecure". But, one thing we'll always have are the 'FITS and style inspo Issa, Molly, and the crew have given us the past 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. Lets get to it!
1.Issa's black cut-out dress with white trim (Season 2, Episode 1)
This was Issa's (played by Issa Rae) post break-up 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)
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 swim suit (Season 4, Episode 7)
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.
P.S. it's on sale and still available in a couple sizes if you want to splurge $386.
4.Kelly's pregnancy announcement dress (Season 5, Episode 10)
The vibrant color, the wide sleeves, the feathers — yes to it all!
5.Basically anytime Issa wore her cream Telfar bag in Season 4 and 5.
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)
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
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)
It's chill, casual, and looks really really comfortable to wear. And that lace-up detail takes it up a notch.
9.Kelly, Molly, and Issa's goodbye party outfits (Season 5, Episode 9)
Kelly's (played by Natasha Rothwell) bustier and red satin suit may be her best outfit of the entire five seasons, Issa's tangerine mini dress 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)
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 colors all weekend.
11.Molly's bold-colored power suits in Seasons 1-5
Yep, all of them!
12.Issa's 'The Last Poets' jumper (Season 2, Episode 2)
Fun fact: The Last Poets are a legendary group of poets and jazzmen based in Harlem, New York. They came together in the 1960's during the Black civil rights movement.
13.Issa's mint pant and cropped blazer set (Season 5, Episode 8)
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)
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 cut-out blazer (Season 4, Episode 8)
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)
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)
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 tee (Season 3, Episode 4)
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)
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 it 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 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)
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)
And the hair crown is the perfect accessory might I add.
24.Molly's Alaia fringe mini dress (Season 5, Episode 10)
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" scenerio outfits on this list, but it's so worth it. Even if real-life Issa didn't get to wear it!
26.Tiffany, Issa, Kelly, and Molly's Halloween costumes (Season 4, Episode 2)
Seeing Kelly dressed up as a 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)
If this list was in ranking starting with the best, just know this gorgeous gown would be number one. Did anyone else cry this entire scene!?
Me seeing the evolution of fashion as the characters become more sure of themselves:
HBO / Giphy
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