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It's Okay to Be Insecure About Your Outfit

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How to Shop Like Insecure's Issa and Molly
By Robyn Mowatt

HBO finally brought a realistic portrayal of educated young black women to prime time with this fall’s addictive run of Insecure. Led by the show’s multi-talented co-creator, Issa Rae, the series centers around two best friends, Issa (Rae) and Molly (Yvonne Orji) as they struggle to find their footing in their love, work, and friendship in and around Los Angeles.

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When the first episode opens, Issa is questioning both her relationship with Lawrence (Jay Ellis) and her career path at a nonprofit, where she’s viewed as the token black girl who can decode pop culture (“Issa, what does ‘on fleek’ mean?”). Molly may be killing it at work as a corporate lawyer, but she’s unlucky in love as she finds something wrong with every guy she dates, refusing to see that she might be the common denominator in that equation. The first season was funny, chaotic, and above all else relatable — not just for the frustrating comedy of errors that ensues, but also for the clothes they wear while it happens.

From the pilot through the finale, each character has a totally distinctive personal style, from Issa’s closet of casual vintage to Molly’s modern power suits to the printed cotton J.Crew of Issa’s coworkers. Everyone on the show, even the secondary characters, mix high and low pieces in a way that feels true to life.

Clothes also help tell the story, whether juxtaposing Issa in jeans and Converse with Molly in silk and designer heels; or showing Lawrence’s confidence grow as his career gets on track by moving from 3XL sweats to slim-cut suits. There are winks to pop culture in the form of graphic T-shirts made by black artists, too. And from Issa’s tees and jackets to Molly’s date-night mini dresses, these are all looks we’d cop.

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To learn more about the clothes on the show, I chatted with Ayanna James, Insecure’s costume designer and Rae’s personal stylist. Here’s what she had to say about the inspiration for each character’s look, where she shopped for them, and other behind-the-scenes details from dressing the cast.

Turns out, emulating the style of your favorite character is not impossible — a bunch of looks are still shoppable.

Shop our favorite looks from the show here >>
The History of High Heels
Click here to watch the video

If you thought that high heels were sexist (much like pockets!)... you might be surprised by their origin story. 

Watch the video here >>
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This weekend's Non-Gift Guide Picks
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Who: Emily Rice
What they do: Astronomer | Blogger, STARtorialist
What they want: Slow Factory NASA Women Scarf, $140

If I had to choose my favorite gift for the upcoming holiday season, it would be one of the NASA Women scarves from Slow Factory. This small, ethical, Brooklyn-based company has designed several previous collections using open-source data (this scarf, one of my favorite "startorial" pieces, uses data from three space telescopes!), but this most recent collection strikes my heart strings as well as my space fancy.

Women have had it tough this year, and this collection features eight wearable reminders that some amazing women have contributed to humanity's exploration of space for decades despite the sexism and racism in their way. Better yet: Combine a scarf with a copy of the delightfully-illustrated Women in Science by Rachel Ignotofsky and a ticket to see Hidden Figures when it comes out early next year!

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Who: Zach Mack
What they do: Owner, ABC Beer Co.
What they want: The Complete Beer Course, $13

Trying to find someone a gift that's both cool and beer-related can be difficult because a lot of what's out there is poorly designed, impractical, or straight up bad for beer. So whenever anyone tells me they're looking to start learning about beer in a structured way, I skip the gimmicky growlers and complicated homebrew kits in favor of this gem of a beer resource.

It has everything from how beer is made, how to taste it, the history of some of the most important styles, recommendations for commercial examples, tips on how to pair it with food, and even a section devoted to helping you find a beer festival that might be of interest. There are a lot of books out there that tackle these things, but none do it as well and concisely as this. And, of course, I like to tuck in a mixed six-pack with it just to make studying a little, uh, easier.

Check out the rest of our non-gift guide picks here. Want to make donations your gift of choice instead? We've got you covered on that front too.

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