How Does Madonna Pick her Outfits? We Asked Her Stylist

Arianne Phillips has worked with Madonna for two decades and has created some of her most iconic looks. She sat down with FLARE to reveal what it's *really* like working with the superstar

Madonna's stylist, Arianne Phillips, posing in white sunglasses and a pink top

(Photo: Rex)

Madonna has changed her look a lot over the last 20 years, but one thing has stayed the same: her stylist.

Costume designer/stylist Arianne Phillips has worked with the superstar for the last two decades, creating her iconic looks in music videos like “Don’t Tell Me” and “Hollywood”, and her costumes for tours Rebel Heart and Sticky & Sweet—to name but a few. And if dressing Madonna wasn’t cool enough, American-born Phillips has also worked with Courtney Love (who makes frequent appearances on her Instagram), Lenny Kravitz and Mick Jagger. Jealous yet?

Apart from making musicians look like rock stars, Phillips is a super successful costume designer. She’s worked on movies including A Single Man, and Girl, Interrupted, and snagged an Oscar nom for her designs in W.E and Walk the Line. For her latest film, Kingsman: The Golden Circle, Phillips styled the likes of Colin Firth, Channing Tatum and Julianne Moore. NBD.

For someone who brushes shoulders with celebs on the reg, Phillips is super humble and down-to-earth. FLARE sat down with the incredibly talented stylist when she was in Toronto to talk about what it’s *really* like to dress Madonna and how she keeps up with the visionary’s evolving identity.

Spill the beans. What’s it like styling Madonna? 

Whether we’re doing a video, a photo shoot, album cover shoot, or preparing tour costumes, usually it’s connected to a larger narrative and an overall story. You know Madonna has been quoted saying she doesn’t wear fashion just to wear fashion. Usually when we’re doing photo shoots, she likes to create a character. So we do that together: we create a character.

Madonna is someone who constantly reinvents herself. Is that a challenge when styling her? 

My job is the perfect merger of art and commerce. It’s creative; we’re telling stories. I always look to be challenged and I don’t like to repeat myself. I was a lot like that before I met Madonna, and even more so having worked with her for 20 years. What we have in common is that we’re both pretty forward-thinking and don’t like to repeat ourselves. Madonna, like me, is inspired by a lot of culture, whether it’s art or film or music or literature. She has such a massive body of work that it feels like every time that she’s kind of done everything, she somehow manages to come up with an inspiration or create music or write a script—she’s writing a script now. I marvel at her ability naturally as an artist to constantly be propelled forward, and lucky for me, I’ve been along for the ride.

You’ve also worked on many films. How does your creative process differ when you’re working on a film set compared to when you’re styling?

I’m not a personal stylist. I’m more like a freelance editor or straight-up stylist when I work with artists like Madonna. How does my creative process differ? Well, it’s intrinsically different because when you’re working on a film, it starts with a script. Costume design is one of the storytelling tools, and our job is to define and create characters based on the script. Clothes define identity and character, and costumes can inform tone and underscore an overall mood of the piece, whether it’s biographical or conceptual or futuristic or fantasy.

With styling, it really depends on what [the project] is. If it’s an editorial shoot for a magazine, usually the photographer and I will come up with a concept and cast it accordingly, and figure out the location. Usually for fashion editorials, it starts with the season, what we’re shooting, the designers, and we tell a story around that. In general, I have a narrative perspective and I’m always interested in a beginning, middle, and an end in terms of telling a story.

Is there a fabric that you stay away from when designing costumes for film?

When working on a film, I have to stay away from fabrics like taffeta or anything that’s going to be super noisy. Usually for film, you have to be sensitive about how an actor sounds when they’re walking because they’re mic’ed. I have a tendency to gravitate towards organic and natural fabrics, but I do also love technical fabrics. I like fabrics that have a nice feel to them.

happy birthday America #musicmakesthepeoplecometogether #americangirl @madonna #jeanbaptistemondino #ariannearchive

A post shared by Arianne Phillips (@ariannephillips) on

Female celebs are often subject to more scrutiny than men when it comes to their red carpet looks. What do you think of the attention women get?

I don’t dress anybody for events—I’m not like a celebrity stylist. In terms of the scrutiny that actors particularly have to endure… I find it cruel and punishing and it has no interest for me, to be honest. I’ve dressed people for the red carpet, but as a rule it’s not something I really enjoy doing because I find [scrutiny] painfully heartbreaking—whether it’s anonymous comments on the internet or bitchy gossip. I don’t find it a positive place to be. It’s of no interest for me.

You’ve also worked with up-and-coming artists like Jasmine Sanders and Lil Yachty. Is it different working with younger stars who are coming into their sense of style compared to those who have been around for longer? Are established artists are a bit more, “This is what I want to wear”?

That’s a really good question. I’ve always gravitated to artists with a strong point of view, who are opinionated, who know what they like, but who are also collaborative. So to me, the artist with the more difficult reputation is always the artist that I find the most inspiring to work with. I think that as they endure the industry and stay in the business for a long time, they learn the pitfalls and the hurdles to avoid, and how to navigate that, whether it comes to what they’re wearing or how they conduct a press interview. I can speak for myself in that it took me many years to figure out my own style and a lot of that comes from getting older.

How would you describe your own sense of style?

I’ve always tended towards a kind of gothic rock-and-roll [look]. I always like to mix it up, contrast-wise, and I dress more for function. I always love accessories; so, I like to wear a basic outfit and then use accessories to express my personality that day. And I also like vintage clothes a lot because I feel like I can express something that you wouldn’t find in every store.

Is there one trend that you’d never be caught dead in?

One trend? There’s a lot of trends. I think the contour makeup trend—I can’t understand that. The spray tan trend… but that’s all makeup. Clothing? There are plenty of things I wouldn’t be caught dead in, but I’m blanking.

What’s the best piece of advice, career or personal, that you’ve ever been given.

Saying no can often craft your journey more than saying yes.

Is there anyone that you would love to work with that you haven’t done so yet?

There are many, many people out there that I would love to work with in lots of different ways. Currently, the person that I’m most focused on working with is a set designer. Her name is Es Devlin and she’s a visionary. We’ve had a few opportunities recently to work together that haven’t worked out. Hopefully I’m going to work with her next year. I find her really inspiring.

2017 Emmys: See How All Your Fave Stars Got Red-Carpet Ready!
Kim K’s Skincare Guru on How to Transition Your Routine to Fall
Watch: Olivia Palermo Shares Her Best Fall Fashion Hacks