Bridgerton's Jessica Madsen Has Some Sage Dating Advice for Cressida Cowper

In Bridgerton's world, the social season is the one time of year young ladies from "the ton" can wear their finest (and most attention-seeking) dresses and display their mastery of etiquette at a series of lavish balls in hopes of securing a marriage proposal. Unfortunately, nobody taught Cressida Cowper how to properly land a suitable match. For two seasons, the Regency era's Regina George has connived, gossiped, and wreaked havoc among her fellow debutantes with nary a man or true friend to show for it. But as we've come to find out in the hit show's third season, there's more than meets the eye with our beloved mean girl, setting forth a villain redemption arc.

"The way Cressida is written is just so delicious," Jessica Madsen says of her character's evolving storyline. Before production began on season three of the Netflix series, Madsen got a phone call from executive producer and showrunner Jess Brownell saying that, alongside #Polin's love story, Cressida would have her own pivotal focus this season. Madsen was both surprised and thrilled at the prospect. Playing the show's ultimate villain is a treat, but getting to peel back those layers and show the human side of her—a side people wouldn't expect—is even sweeter.

Cressida, it turns out, has some emotional baggage, a cold mother, and a cruel, unforgiving father. As the only child, all attention is on Cressida to marry in order to secure her family's wealth. No pressure. Needless to say, there isn't much love going around the Cowper's dark and austere residence, which explains her unkind and abrasive nature toward others. Thanks to a blossoming friendship with Eloise Bridgerton, however, transformation seems to be afoot for Cressida.

We talk to Madsen about Cressida's roller coaster of a season, the costumes and hair design that blew her mind, and what she hopes is next for her character.

Jessica Madsen sits on staircase in red satin halter dress by Galvan.

(Image credit: Kirk Truman; Styling: Galvan dress; Jessica McCormack earrings and ring; Gianvito Rossi shoes)

Let's talk about Cressida Cowper's journey. She's always been our villain, but this season, we get a peek behind the curtain to understand why she is the way she is. How has it been for you to go on this journey with her?

Very exciting. … We see such a different Cressida at the start of this season. Her forming a friendship with Eloise and them holding up mirrors to each other, they are growing in different ways. We do see that it takes another shift, and then it pumps up, and she's full blazing into how she's going to get herself out of the situation she's in. It's a real roller coaster of events that take place over the season for her—that's for sure.

What do you enjoy about coming back to this character each season?

The way Cressida is written is just so delicious, and I love the Regency era and how they speak. It's like a tennis match, all of these scenes we have. It's a delightful show to come back to. I absolutely adore working with everybody, and I feel really confident and comfortable on these sets because I've known these people for a long time now. It's been a really great place for me to grow as an actor and to learn as an actor, too, in a really supportive environment.

What has the response been to Cressida's story so far in part one?

It's been amazing to see people's response after the first drop of the season because people are like, "Oh wow, I'm really feeling for her, and I'm seeing a side of her I never expected to see." That was great, and I felt like I had done her justice and what I wanted to do. I was a little nervous that it might not read in a genuine way. It felt genuine when we were doing it with Claudia [Jessie], but you never know how it's going to be received. So I was like, "Phew." I was really thrilled with the response.

Jessica Madsen poses wearing two-piece set by Simone Rocha with 3D rosette detailing.

(Image credit: Kirk Truman; Styling: Simone Rocha top and skirt; Lily Gabriella earrings and ring; Gianvito Rossi shoes.)

She befriends Eloise despite having mocked her earlier and also being Daphne's nemesis. Why do you think she attached herself to Eloise?

I think she's always been one for setting herself up to achieve something and wanting to win. It's like, "She'll be next. I'm going to be friends with that one and see how that goes." These girls are young. They are still trying to figure out who they are. A lot of times, we figure out who we are by who we are also in front of and who we are talking to and learning from, so I think she is really intrigued by Eloise.

She does very truthfully say, "I did try to befriend you in your first season out." If you look back at that scene where she walks up to [Eloise], you're like, "Is that really your attempt at genuinely trying to make a friendship because that's a bit weird." But then when you hear that, you're like, "Oh, that was her attempt at doing it. She's doing her best with the limitations of how she's been brought up." I think she was just like, "I'm going to pick her and see," and she was actually like, "Wow, you're kind of amazing" and starts learning a lot about herself, and it opens up a whole new perspective on life.

Was it fun getting to play out that dynamic with Claudia Jessie?

Yeah, [Cressida and Eloise] have these really wonderful chats, and Claudia and I don't do small chats. In our personal lives, we also really like to contemplate things and have deep, meaningful conversations, and we see these two girls doing the same. They are open and receptive to that—they're not defensive. They are really curious, and I think we see a really beautiful curiosity between the two of them of what life is like for the other.

Cressida doesn't go, "How dare you say that" and shut down. She's like, "Oh, that wasn't nice? I thought we didn't like her. What am I supposed to do then?" … Be kind. You don't have to be cruel just because you don't like somebody. It was really wonderful working with Claudia. She is a gift as a human being and as a friend and also as an actor to work with. She's so connected. You can't help but be present with Claudia. She commands it. Just when she looks at you, you're like, "Okay, we're here."

Jessica Madsen poses in front of sheer white curtain.

(Image credit: Kirk Truman; Styling: Del Core dress; David Morris bracelet and ring)

We have to talk about Cressida's style this season. She's definitely peacocking with all those big sleeves and lots of embellishments—like pom-poms, rosettes, and ruffles—in an effort to attract an eligible suitor. Can you take me inside your fittings for Cressida?

Walking into that fitting room is like going into a candy store. I go in, and I'm like, "Whoa!" In life, you have expectations of how cool something could be, but John [Glaser] and George just break that expectation every time you walk into the room. … How is it possible for you to be this talented and artistic and creative? It's blowing my brain. They outdid themselves with every costume that came and so varied … and really flamboyant as well. I love you saying the peacocking because that's exactly what it is. She's showy, and she's being bold.

I actually found the fittings quite emotional because [the clothes] are made for your body, and it's amazing. There's not many times in life that you wear something that absolutely fits you like a glove. It feels like a second skin. These costumes bring so much of the character to you. If someone said, "Okay, you have to run a scene or rehearse a scene without costume," I'd be a bit like, "Where is she?" The minute they're on, I'm like, "Here she is." Also, it was great to see [her wardrobe] develop. I'm always seeing Adjoa [Andoh, who plays Lady Danbury] in these beautiful coats and have been envious of them. I wanted to wear them. This season, I had my own coats for Cressida, and I was like, "Wow, this feels mature and feels brave and feels like more independence to her." By the end of it, she does feel like an adult. Emotionally, there is still a lot of innocence in her, but I felt very much like she was adulting.

Do you have a favorite look of hers this season?

Yeah, it's the red dress. I love the color red. It's not a color I wear very often, but it's a color now where I'm like, "I want to wear red."

I interviewed Nicola Coughlan for season one, and she described the fashion in the show as the Bridgertons being Chanel and the Featheringtons Versace, which I loved so much. Recently, she said she would now describe Penelope's style more like Prada. What designer would you assign Cressida?

With the puffy sleeves, I feel like it's giving John Galliano. I've adored him since I was younger. I was really into fashion, which I still am, but I was obsessed with it when I was a kid making dresses with hair and weird things like that. Not real hair—don't worry! I got so deeply fascinated by him, and this season, I walked in [to the fitting] and was like, "John Glaser, it's giving John Galliano."

Jessica Madsen wears blush Stella McCartney dress with feather detailing.

(Image credit: Kirk Truman; Styling: Stella McCartney dress; Agent Provocateur bodysuit; Boodles earrings and ring; Christian Louboutin shoes)

Every time we see Cressida, she has a different intricate hairstyle, and I read one of your wigs was called "the crispy." Did you have nicknames for your other wigs?

It was called "the crispy!" Someone named it crispy because it looked like pasta. But I don't know if we did name any of the other ones. That was one of the first ones I wore. … There were so many designs this season I couldn't quite believe that [key hairstylist] Grace [Gorman] could just continue to make so many different ones with varied designs. There was a top hat that was made that didn't get used that was really cool.

A top hat made of hair?

Yes, like the hat that Lady Danbury wears. In the end, they were like, "It's not quite right." But hey, maybe [Cressida] will come back in a top hat. Who knows? I'm not sure what my favorite headpiece was. It's all kind of blended into one. Oh, I have a tattoo on one of them in the second half. It's actually tattoos printed onto it, so that was pretty wild. They are incredible. They are, in my eyes, the stars of the show.

You posted a photo on Instagram of yourself at 5 years old in a very Cressida-esque look. Would you say the two of you have a similar affinity for statementwear?

Absolutely. I always dressed up as a kid. My mom was a model, so she had these amazing clothes she was given when she was working, and I was always putting them on and doing fashion shows as a kid. I was quite literally walking up and down the living room doing fashion shows in very odd things. It's funny because it reminds me of… People have made a lot of clips of Cressida's looks with, like, Crocs on the shoulders. Somebody even had a dog, which I loved, and the grapes. I was like, "Yeah, 100%, that was me as a kid, putting anything onto my body to see if I can balance it."

Jessica Madsen dances in emerald green one-shoulder dress by Sabina Bilenko.

(Image credit: Kirk Truman; Styling: Sabina Bilenko dress)

If you could give Cressida some dating advice, what would it be?

Just be you. In an ideal world, I'd be like, "Babe, take a year out. Do some therapy, really think about who you are, heal that childhood trauma, and then go for it." But she obviously doesn't have that opportunity. If she could open up the way she has with Eloise, she would. Whether she would find love with someone like the Bridgertons have always looked for, I think she could still find a companion who she would be really happy with. Look, I would love for her to find love, but in those days, that was something that was really rare. I would like her to find a safe place, somewhere emotionally safe for her to be.

Everyone's talking about who will be the focus next season. What do you hope to see in terms of Cressida's story?

I would like to see her make amends with Eloise and with Pen. I would really like to see the two of them. It would be cool to understand what happened there. They've both had a similar journey in some ways. They both understand what loneliness is, and they've both had it out for each other. But we don't really know why yet. Nic and I have spoken about it, but I think that would be cool to see. I would like her to find happiness. That, or I'm like, "Make her go full villain." That's just me liking to be all dramatic. I don't think that's right for Cressida.

Catch up on Bridgerton season three, now streaming on Netflix.

Photographer: Kirk Truman

Stylist: Harriet Nicolson

Hairstylist: Paul Jones

Makeup Artist: Beth Long

Venue: Kimpton Fitzroy London

Executive Director, Entertainment

Jessica Baker is Who What Wear’s Executive Director, Entertainment, where she ideates, books, writes, and edits celebrity and entertainment features.