If a pop concert wants to scale every possible height, it needs shoes – lots of them. As in, 700 pairs.

That’s the approximate number that stylist Arianne Phillips and her team tallied for one particular Madonna tour, including the footgear worn by various backup dancers, musicians, and, of course, the headliner herself.

Madonna’s crew might also have upwards of $30,000 in Swarovski crystals on hand, as well as custom garments from the likes of Tom Ford, Miu Miu and Jean Paul Gaultier, all of which must withstand months of travel and intricate choreography. That could mean the sequinned kimono she wore in 2015, or the white ABBA-inspired pantsuit she sported in 2006.

“Designing a tour, especially a Madonna tour, is one of the most exhausting, impossible mountains to climb,” Phillips says. “It’s also the most gratifying, thrilling, and just incredible experience.”

The queen of pop, who has raised the bar for eye-popping live shows, is set to embark on The Celebration Tour on 14 October following a health-related postponement. It’s Madonna’s 12th roadshow and the first built around the greatest hits of her 41-year career. Phillips was Madonna’s stylist on six of those stage spectacles, from 2001’s Drowned World to 2015’s Rebel Heart. In between, she did many of Madonna’s photo shoots, album covers, music videos and red-carpet ensembles — all while remaining a top-tier costume designer, whose movie credits include Walk The Line, A Single Man and Once Upon A Time in Hollywood.

Phillips met Madonna in 1997 when Courtney Love sent Phillips’ portfolio to Madonna without telling her, thus initiating “one of the most important relationships” of her life. When Madonna was assembling Drowned World, which came after an eight-year touring gap, Phillips embraced what an endeavour of that magnitude entails: roughly 15 weeks of rehearsals, a coterie of assistants and technicians, and constant moving parts that need synchronising. Madonna’s shows are usually split into four acts, each with a distinct theme and aesthetic. About 12 weeks before a tour begins, Phillips would develop the costumes alongside Madonna and the show’s director. She presented sketches and mood boards, invited couturiers to contribute outfits, and modified the clothes to accommodate quick backstage changes. Sometimes Madonna called her a few months after a tour had launched to ask for wardrobe updates so she doesn’t get bored with what she’s wearing.

“Working with her really taught me a lot about working hard, researching, and having purpose and meaning,” Phillips says. “She expects you to bring something to the table. She’s very collaborative, and that’s where the pressure comes in. She will not spare any expense or attention to detail. Before a dress rehearsal, we’ll do a lineup of all the dancers in costume and I’ll walk down the line with her. She’ll notice if a button is out of place. That gives me life as a designer. She doesn’t miss a beat.”

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Phillips On 5 Iconic Madonna Music Video Looks

Ray Of Light (1998) – “One of the things she told me initially is, ‘I don’t wear jeans.’ But she never said she wouldn’t wear a jean jacket. With all that beautiful fast-motion footage, I thought it was a great opportunity to strip her back.”
Don’t Tell Me (2000) – “This was a collaboration with Dsquared2. It was an outsider’s perspective on Americana. The idea of Madonna doing a cowboy thing was weird enough, but we were turning it on its head. She was totally up for it. I have to say, the cowboy hat became a little bit of the bane of my existence because it became tour merch. I thought it was great as an ironic thing for her to wear, but she really got into it. We would have these little arguments. I’d be like, ‘No cowboy hat! We’ve done it enough.’”
American Life (2003) – “She’s making a statement. At that time, it seemed right. That was a very scary time [with the start of the Iraq War]. Madonna has famously worn menswear and strong silhouettes from way before my time with her. That’s who she is.”
Hung Up (2005) –  “This first came to be in the Confessions On A Dance Floor album cover we did with Steven Klein. The Hung Up leotard is a vintage leotard I bought at a flea market. It has a crepe wrap top made for us by a London designer, and she’s wearing a sequinned vintage belt that I bought at some thrift store. There’s a continuity with the album cover, the music video, and the tour visuals.”
Girl Gone Wild (2012) –  “This video was directed by Mert [Alas] and Marcus [Piggott], the incredible photographers we had shot the MDNA album cover with. The concept and look were inspired by the supervixen Tura Satana, who starred in the Russ Meyers film Faster, Pussycat! Kill! Kill! Her backup dancers are from the Ukrainian group Kazaky, who are known not only for their Eastern European club hits but for their incredible dancing in high heels. We evolved the look for the opening of The MDNA Tour. We shot the video two days before the Oscars when I was nominated for W.E., the film she directed.”

Matthew Jacobs is a freelance entertainment journalist who also writes for Vulture, The Cut, Vanity Fair, The Hollywood Reporter and The Daily Beast

Arianne Phillips On What It Takes To Style Madonna’s Elaborate Tours

By Matthew Jacobs

Oct 03, 2023

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