What It’s Like to Dress Two of TV’s Biggest Girl Bosses, Annalise Keating and Olivia Pope

What It’s Like to Dress Two of TV’s Biggest Girl Bosses, Annalise Keating and Olivia Pope
Byron Cohen/ABC; Mitch Haaseth/ABC

When we think of the most powerful female characters on TV, Scandal’s Olivia Pope and How to Get Away with Murder’s Annalise Keating are at the top of our list. Both women are strong, politically-minded, and aren’t afraid to go after what they want when it comes to their careers and personal lives. And each character has her own fierce wardrobe, to boot.

As of this TV season, both Olivia and Annalise are styled by the same woman: costume designer Lyn Paolo. She's dressed Kerry Washington in Olivia's Scandal power outfits since 2012, and she was most recently tapped to take over wardrobe duties on Viola Davis-helmed How to Get Away with Murder for the drama's third season, which premiered last week. But despite the fact that she dresses two of Shondaland’s key characters, don’t expect to see Olivia and Annalise wearing similar looks during ABC's TGIT lineup any time soon.

“I’m trying hard for that not to happen,” Paolo recently told InStyle. “It’s a tricky line for me, because I think everyone will be watching to see if Annalise is dressing like Olivia—and one hopes she isn't. But I’m only one person and there’s only so many things out there in the world. I just hope that they look distinctly different, because they’re completely different people—apart from the drinking. I’m fascinated that they both drink, and yet they can both get up the next morning and go to work!”

Byron Cohen/ABC

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Of course, the characters’ looks—and drinking habits—go hand-in-hand with what's going on in the worlds around them. “How to Get Away with Murder’s creator Pete [Nowalk] is telling one story, and Shonda [Rhimes] is telling another story,” said Paolo. “I try to make every single character their own person within the story and show how they’ve evolved within it, so I’m hoping that the two ladies are nuanced and that they don’t look alike—although they are both very strong and I love each character dearly.”

Off-camera, Davis and Washington are as different as their characters. “Viola is less interested in fashion than Kerry, I think,” said Paolo. “If she loves something, she loves it—but she looks at it as an actor. It’s for Annalise, it’s not how Viola dresses. The same is true of Kerry, but Kerry practically always has a magazine in her hand and is looking at fashion. If she hadn’t done this for a living, maybe she would have even gone into the fashion world. She loves clothes, and we’re fashionistas—we get giddy when we find something that we love.”

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While she may not be quite as style-obsessed as Washington, Davis keeps things just as lively on set. “Viola rocks her performance, and we’ve spent a lot of time laughing in our fittings,” said Paolo. “She’s a theater-trained professional, but she’s a total riot—I watch her and she just cracks me up. She has great trust in the process, and it’s such a gift from an actor when they say, ‘I’m in your hands.’ Fashion may not be too high up there on the list for Viola, but she loves beautiful things, that’s for certain.”

Nicole Wilder/ABC

And a few special pieces manage to catch Davis’s eye on the HTGAWM set. “She absolutely loves the coats,” said Paolo. “There’s a little Prada dress that she was pretty mad about, too.” Davis may even wear one of Paolo’s finds off-camera in the near future. “There’s a great black-and-white Altuzarra jacket that she’s obsessed with,” said Paolo. “She may borrow it for an event—actually, it reminds me a bit Olivia Pope.”

 
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