Interview with OUR FLAG MEANS DEATH Costume Designer Gypsy Taylor

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Max’s hilarious and surprisingly heartfelt queer pirate comedy Our Flag Means Death just wrapped its pretty much perfect second season (listen to our latest podcast for our thoughts on why it worked so well). Given the show’s exploration of queer, drag, and nonbinary characters, not to mention the racial, ethnic and body diversity that encompasses the show’s large cast, all set in a classic period piece moment in history, we simply had to sit down with the show’s insanely talented costume designer Gypsy Taylor to get the lowdown on how she tackled all of these glittering, fabulous pirates in all of their diversity.

TLO: Hi, Gypsy, thank you so much for making the time to talk to us about your creations for the second season of OUR FLAG MEANS DEATH on HBO Max. We’re huge fans of costume design and we just love all the attention that costume design is getting right now.
Gypsy Taylor: Oh, thank you.

TLO: So, let’s start by talking about your approach in general. Did you do any research in terms of the Golden Age of Piracy?
Gypsy Taylor: That’s 100% where I started. What happens on every job I get, there’s often a period that I have to think about straight off the bat, and I go, well, where do I begin? So on this one, I began with The Pirate History podcast, which was all about the era of the Gentleman Pirates. And I would start listening to that on my way into work every day and kind of get the sponged information into me so I could start thinking about that era and what happened and the real stories that came from it. And so it always began with the historical and the 18th century period. And then once we got rolling, we were able to put our own spin on it to make it a little queer, a little punker, a little bit out of the ordinary.

TLO: How did you approach dressing the queer characters in a way that felt both correct to the time period, but also clearly queer?
Gypsy Taylor: Yeah, I love that. That should be my middle name, clearly queer.

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TLO: For example, Lucius Spriggs [played by Nathan Foad], he’s dressed for the time period, but at the same time, there’s such a contemporary take on his look.
Gypsy Taylor: All those jeans look so beautiful on him. This was when I spoke to the director, David Jenkins. He was like, Lucius has been lost at sea, he’s been through some trauma, he’s dealing with some shit. And he was so gentle and sweet in the first season, and he is basically been tortured. So he’s come out of it on the other end, sort of the James Dean stereotype. So the minute David Jenkins told me that, I was like, ‘oh, what would I do with an 18th century James Dean?’ And I was like, ‘well, robably just be a white T-shirt and blue jeans.’ And I looked into some 18th century jeans that were made in that time, and sailors actually used the sails to sort of make their pants like that cotton drill. That was a historical fact. So we sort of took liberty there and gave it that James Dean, 18th century twist on his jeans. And then I did things like lowered his neckline a little bit just to show off his chest and give him a little…kept his little flouncy tie around his neck, and he made a character choice to take on smoking. And when we see him first in his Chinese uniform, he’s ripped the sleeves off and rolled them up, kind of like a fifties motorcycle gang member.

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TLO: You can’t stop looking at him. That’s the other thing we noticed and paid attention to: the costumes change when Zheng Yi Sao, the Chinese pirate queen [played by Ruibo Qian] takes over. All of the pirates start wearing clothes with Asian and Chinese design elements.
Gypsy Taylor: Well, we started with Captain Zheng and her fleet. So this was a historical character in time, and she was like the most badass pirate. She had a fleet of something like 250 ships with all of these women working for her. And I thought what would be really nice if they had a really simple sort of uniform that was just light and versatile and utilitarian so that they were comfortable, they could do their job, a lot of thought went into what that uniform might be. And then through the script with them arriving on the boat, to me, it felt right to just pack their clothes away and they pay their sort of respects to Captain Zheng by becoming part of her crew, and she assigns them roles. And so they donned the uniform too. And I was always very conscious to be culturally respectful as well. I didn’t want to take the piss out of putting them in a Chinese bit and have it be wrong, but it just felt right that Captain Zheng was looking after them and embracing them and making them part of her crew.

TLO: They’re so beautiful. The layered fabric, the texture, the knots…
Gypsy Taylor: Yes, they’re beautiful, we had this crafts person, Melissa, she would sit there and do a lot of my knot tying and my knitting and anything to do with knots and fingers and small details. She sat there for a week just making those tiny little knots that go on everybody’s costumes. And we had two of those costumes, so it was amazing.

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TLO: Also, the character Jim played by Vico Ortiz, you did such a good job making sure that their non-binary identity was reflected in the costumes. What were your choices?
Gypsy Taylor: With Vico I wanted to make sure that they were comfortable and happy, and we really chatted a lot about what the progression was of the character of Jim. And again, Jim has been under the ruling of Blackbeard and been through some horrible things, seen some horrible things, and has also had to don a costume to be part of his gangs so that he sort of accepts them and doesn’t pick on them so much. So that’s all. We kind of infiltrated that Mad Max look throughout the new crew, which was Frenchie and Archie and Jim. And when we started with Jim’s costume, it’s a huge difference from season one, but what I really wanted to make a point of was making a really wonderful binder and building the costume on that binder. So working with Vico, we came up with the most beautiful comforting binder that they could ever wish for. And then we incorporated that look with all these ropes and made sure it was the same height, so we saw a little bit of belly. So that’s where we began with that. It was sort of the Mad Max thing and making sure that they were comfortable in their binder.

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TLO: What we also love is how the costumes ilustrate so well the depevelopment of the story and the characters. In season one, for example, the character Stede Bonnet [played by Rhys Darby] is impeccably dressed, not one wrinkle or smudge on him and in season two everybody is miserable, looking dirty and wornout and you can see that on every costume, you also incorporated a lot of leather and a more S&M tone to the looks.
Gypsy Taylor: Yeah, yeah, totally. I think my most S&M look that I went with was Anne Bonny. So they’re in a relationship that’s really similar to Who’s Afraid of Virginia Woolf?, that real sadistic — they kind of get off on torturing each other. So I really wanted to incorporate that sadistic look with those two and had that beautiful fetish leather corset on Minnie Driver and gave him some gorgeous detail, little chains and things like that to incorporate that. I kind of digressed on that S&M.

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TLO: Now, let’s talk about one of our favorites looks, the drag look the character Wee John Feeney [played by Kristian Nairn] wears.
Gypsy Taylor: And did it make you think of Divine?

TLO: Yes, the hair and makeup, everything.
Gypsy Taylor: Good. Yeah, that was the plan. It was scripted really early on that he was going to be in drag, and then there was talk of maybe there wouldn’t be time to see it, and it kind of went back and forth a bit. So I was like, ‘Please, please let me put Wee in drag.’ It’s my dream come true. And he’s a large guy. He’s like seven foot tall, and I was just like, give it to me, I want it. So we give him all the padding, the boobs and the hips, and we corseted him a little bit. And I wanted you to read it instantly as Divine, because I’m a huge John Waters and Divine fan. So I wanted to give it that Babs Johnson silhouette with the fish tail. But then I’ve always known that also Ursula from The Little Mermaid was based on Divine. So I thought, why don’t we incorporate that sweetheart neck line and sort of do a play on Divine and Ursula to come up with the Wee John, sort of a full circle, sea enchantress moment. And then I was thinking, where would we find things that sparkle that he’s been able to have access to? So we covered the whole top with abalone shells and he’s got a fish hook earring with a shell. So anything that sort of sparkled. And Nancy Henna, the hair and makeup designer was like, ‘well, they had access to indigo, so that would’ve been the blue eyeshadow.’ So all the things, and then the boa is made out of seaweed and all these wonderful things they would’ve found at sea, but obviously a bit of rhinestones was pushing the envelope a little bit.

TLO: We love that combination of research and creativity producing fantastic and unexpected results.
Gypsy Taylor: I’m always influenced by pop culture and everything that’s influenced me as a designer. So whenever I get the chance to infiltrate that into my design, that’s very much my aesthetic.

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TLO: We have to talk, of course, about the most stunning costume of the season. The velvet suit worn by the character Stede Bonnet. We cheered when we saw it, it’s genius from a costume design perspective.
Gypsy Taylor: Thank you. I saw a really funny meme that just said, “A million queers just found their Halloween costume.”

TLO: It’s such a fantastic piece of costume with all the embroidery, textures and symbolism, and the way Rhys Darby worked it and played it up.
Gypsy Taylor: Oh, he lived for that outfit. So with that one, we started with what was the ship that they were raiding? They were often at sea raiding European ships. And the director said, what if it’s a Spanish ship? So I started there and I was like, okay, what would be this Spanish opulent thing? And Stede, like you were saying in season one, he was used to opulence and used to having velvet and silk and all these lovely fabrics, but in season two, he is lost. Everything. Stede was saying to me like, “Gypsy, can I have a ring? Just one ring?” And I was like, ‘no, you’ve lost everything. Unless you steal it, you’re not allowed to.’ So that was the moment where he’d seen a flashback to his old life, and he’s like, oh, red velvet and embroidery and Swarovski buttons and all these gorgeous opulent things.

And I just went more and more, every trim we had, we put on it, we lined it in all these different linings. Everything was just crazy cool. So we started with a Spanish matador as the base. That’s what gets that dramatic shoulder and that short cropped coat, those really tight high pants. So instantly that was sexy to me, but I was like, ‘how do we put an 18th century twist on that?’ So I took a reference from 18th century Dandies where they had those really long tails, and the minute that we put Stede in that in the fitting room, he stood up straight, put his shoulders back, sucked his tummy in, and lifted his butt. And then he was spinning around and playing with the tails, and I was like, we’ve done it. This is great. We’ve nailed it.

TLO: It’s such a wonderful moment in the season and it’s such a wonderful moment for costume design because it’s one of those costumes that you create and it’s so much part of the story. All the other pirates, everyone is talking about it.
Gypsy Taylor: And they’re like, get rid of it. But did you notice he kept the shirt? He just wanted to hang on to just a little bit of lace.

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TLO: The women also look amazing on the show. Leslie Jones looks incredible as Spanish Jackie, her costumes are gorgeous.
Gypsy Taylor: And we had a lot of women to play with this season, a lot of broads, a lot of bad asses. So that’s my favorite genre as well. I just made sure that they were all looking as hot as they could possibly look. Leslie Jones was so fun. She’s such a huge character in real life, and in the first season she was very much influenced by Prince and all that velvet and lace and pearls. And this season we kind of wanted to up it and make her just a little bit sexier with all of her husbands. So I had a lot more cleavage, and she was sort of a mix between Sheila E. meets Tina Turner and Mad Max.

TLO: You can tell that every detail in every costume was meticulously thought out.
Gypsy Taylor: I’m glad you noticed all the detail. I often work in film, and so film is a different level of detail. You are thinking about it on the big screen, and that button you choose will be five feet high. And whereas on tv, I dunno if people are going to watch it on their phone or on a big screen tv, but I always apply that mentality of what if it was on the big screen and that detail and that level of care, because I think everyone noticed it, especially the fans, they pause and zoom in and just get every detail and soak it up. So I’m kind of happy I thought about all of that in the process.

TLO: The great thing about our technology today is that a lot of people watch shows on their computer and phones, and you can see so much more now when you zoom in, like you said. We have talked to costume designers about how you can see more details now like a shoe, a bag or a belt.
Gypsy Taylor: You’ve got to think about everything. And it might not get on camera, but you’ve got to think of it just in case it does.

TLO: It seems to us, this show in particular, just listening to you talk about it, it sounds like it must be a costume designer’s dream just because it covers a specific time period, but then it also covers queerness and gender non-conformity and racial and ethnic diversity and size diversity. So there’s just so much for you to play with there.
Gypsy Taylor: And ultimately it’s a love story. So you get to put love into all of the things that you just said. And for me, that’s the greatest thing you could ever do, tell a story and have it be a joyful story of love and acceptance. And I hope that that comes through in every choice that I make. And it’s definitely a dream job for me. It doesn’t come along that often. I’ve worked on some magical projects in my time, but this one is, I’m not just saying it because I’m talking to you. It’s like one of my most favorite projects I’ve ever been a part of. So I’m really, really chuffed.

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TLO: It sounds like you benefited a lot from working with amazing actors really understanding the importance of costumes. The costumes took season two to a whole new level.
Gypsy Taylor: Thank you, that means the world to me. I was so proud to be a part of this production and reading the stories and then just getting to play and play with these wonderful actors who just embodied all of it and took on the queerness, no matter whatever, what they do in life. So it was just beautiful.

TLO: Well, fingers crossed for season three.
Gypsy Taylor: Yeah, fingers crossed. Wouldn’t that be great? I’d love that.

TLO: Thank you so much for your time and congratulations again on such a great job.
Gypsy Taylor: Thank you. Lovely to chat with you both.

[Photo Credit: Nicola Dove/Max]

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