The story behind Madonna’s most iconic ’90s looks, straight from her hairstylist: ‘She loves transforming herself’

With the sequel to her 2005 “Confessions on a Dance Floor” album finally here, Madonna is revisiting her own legacy — and so is one of her go-to glam pros.

Celebrity hairstylist Garren worked with the pop star on some of her most iconic ’90s and early-2000s looks, helping refine her ever-evolving image in the process.

“I just love making characters out of characters,” he told Page Six Style. “She loves transforming herself.”

After first connecting on the set of an Italian Vogue shoot, the duo became “like lock and key” for over two decades, with Garren often offering candid feedback on more than just the Queen of Pop’s hair.

Garren transformed Madonna’s hair for several high-profile magazine covers, including this 1991 issue of “Rolling Stone.” Rolling Stone

Garren (pictured backstage at NYFW in 2019) has also worked with a who’s who of Hollywood over the years, from Victoria Beckham to Kim Kardashian. Getty Images NYFW: The Shows

“I think that’s what she liked about working with me, because she always said, ‘Garren, what is wrong with the way everything looks?'” he laughed, recalling a time he commented on her outfit at the Venice Film Festival — and wound up accompanying her to a Tom Ford store in Canada instead.

“[She said], ‘You’re coming to Toronto with me … because you’ve got to help me pull my look together to be look more serious,'” he recalled.

Garren often sourced style inspiration from another era, collecting tabletop tomes about Old Hollywood. (“We would drag the books to the shoot, and I would tag the pages,” he recalled.)

Given Madonna’s now the blueprint on plenty of fans’ vision boards, we asked the famed hairstylist and R+Co and R+Co Bleu co-founder to dish on three of her most iconic ‘dos — and which modern products he’d use to re-create them.

Marilyn Monroe-inspired Vanity Fair cover, 1995

Madonna had a blond moment on the cover of Vanity Fair in 1995. Vanity Fair

“[She was wearing] her own Harry Winston jewelry that she bought on her own. Those were the days when she would come to the studio by herself, and maybe her publicist would stop by to just say hi and then leave.”

R+Co Bleu Blonded Brightening Masque

R+Co Bleu

If you’re a “Material Girl” looking for products to care for your blond locks, Garren said he would use this hair mask — plus the Blonded Brightening Shampoo — to create this look today.

“Her hair was bleached out to this pale yellow, but it didn’t have that platinum shine to it,” he said, explaining that the luxe products would help “make it more shimmery.” 

MTV VMAs, 1995

“It was supposed to have a fur coat, but it was way too hot that night,” Garren recalled of the superstar’s iconic Gucci look. Ron Galella Collection via Getty Images

“I had a fall from the late ’80s that I just pulled out of my closet. I have a stash of hair that I keep, and I have a whole area that’s Madonna hair. She [was inspired by] a picture of Catherine Deneuve walking through the lobby with her hair pulled up. I went for it and it really elevated her and took her to another level.

“It made Courtney Love very uncomfortable that she looked so glamorous. Madonna was like, ‘Oh God, here we go. She’s gonna wreck me … don’t let her touch my hair.'”

R+Co Bleu Cult Classic Hairspray

R+Co Bleu

While Madonna was wearing a hairpiece for her much-discussed VMAs appearance, Garren said he’d incorporate this spray to creat a similar style.

“I like the way it feels over the hair,” he said. “When you brush it out, it has a ton of memory.”

“Sex” book and “Erotica” music video, 1992

Garren was also Madonna’s go-to on set for music videos like “Erotica.” Youtube/Madonna

“We just had so much fun for four weeks. When you look at the ‘Sex’ book, you think, ‘Oh my God, how did that happen?’ But we were laughing through the whole process because every situation was set up.”

R+Co Bleu Optical Illusion Smoothing Oil

R+Co Bleu

To get the slicked-back chignon from Madonna’s “Erotica” video, Garren recommends applying this oil for a “glassy” look that stays put all day.

“Oil usually takes the wave out or the curl out, [but] we wanted something that would just coat over the hair,” he said.

This interview has been edited and condensed for clarity.

Why Trust Page Six Style Shopping

This article was written by Hannah Southwick, Commerce Associate Editor for Page Six. Hannah spies deals on actually affordable celebrity-worn styles, puts celebrities’ brands to the test and finds the beauty products that keep stars red carpet-ready. She consults stylists and industry pros — including celebs themselves — for firsthand product recommendations, trend predictions and more. In addition to writing for Page Six since 2020, her work has been featured in USA Today and Parade.