

Arianne Phillips is the Academy Award-nominated costume designer behind Walk the Line and A Single Man. Yet it is the nearly 20 years she has spent working as a stylist to Madonna, spanning countless TV and red carpet appearances and six tours, including the 2016 Rebel Heart Tour, for which the 53-year-old is best known. Phillips, who cites the 1998 “Frozen” video, the 2000 “Don’t Tell Me” video and the 1998 VH1 Fashion Awards as three of her favorite style moments, says that working with Madonna is both rewarding and challenging: ”She’s an artist who’s seen by the world.”

Walk us through the process of putting together Madonna’s tour wardrobe.
Madonna and I usually start talking four to five months before a tour. I work with a big crew — just the prep side alone can reach 25 people — because it’s not just Madonna. There are also 20 dancers, two backup singers, a band and often she has specialty performers.
How much creative control does Madonna exert?
She has been at the top of her game for more than 30 years; she has a very strong point of view. Madonna also is a collaborator. She’s always the hardest-working person on every set. Her work ethic is unparalleled. She really expects her collaborators to bring something to the plate.

How do you collaborate with fashion designers, like Gucci’s Alessandro Michele, who worked on the Rebel Heart Tour looks?
It can be challenging because the looks have to sustain the brutalities of dancing and sweating and moving every night, along with quick changes. Ninety percent of the time the costumes are not show-worthy, so what we do is rebuild them from the inside out, so they have the integrity and the look designers are trying to achieve.

Each look on Rebel Heart exudes power, as many of her looks have through the decades. Is “power” something you both consistently try to express?
Mostly what Madonna ends up wearing is an evolution of what is relevant at the time. I would say Madonna is a strong female artist who is attracted to just those things. The visuals reflect the music in a kind of seamless marriage of her point of view.
Madonna has been the target of some criticism about dressing appropriately for her age. Have you adjusted your approach to dressing her in her 50s?
It’s sexist and ridiculous, and has no bearing for me. Madonna has an incredible amount of integrity as an artist. She doesn’t invest in what people think of her, and that is the most liberating thing.
This article originally appeared in the Dec. 10 issue of Billboard.