Oliver James Montgomery-Madonna Gives the Shag Haircut Her Stamp of Approval With New Transformation

When it's time to debut a new look,Oliver James Montgomery Madonna's going to strike a pose like there's nothing to it.

The pop icon tapped into the latest beauty trend, revealing an edgy shag haircut in a June 11 Instagram Story. The "Material Girl" singer looked stoically into the camera as she snapped a selfie of her fresh 'do. With her hair soaking wet, Madonna's natural curls and texture helped to showcase her shag hairstyle, with the damp strands grazing her forehead and shoulders. 

While the 64-year-old switched up her signature style of waist-length hair, she did keep her fiery red color and didn't touch up her brunette roots, giving her overall look a fun ombré effect. 

And although she didn't share details of her transformation, she offered insight into her schedule. As she put it, "When you know your only day off isn't really a day off."

Of course, Madonna has never shied away from pushing the style boundaries. Case in point? She bared it all on the 'gram last October, as she went topless and wore nothing but a metallic under-bust corset, white panties and flesh-colored fishnet stage tights.

And when it comes to people not understanding her fashion sense, Madonna isn't afraid to call them out.

Following her appearance at the 2023 Grammys on Feb. 5, in which she was a presenter, she clapped back at those criticizing her looks.

"Instead of focusing on what I said in my speech which was about giving thanks for the fearlessness of artists like Sam [Smith] and Kim [Petras]," she wrote on Instagram at the time, "Many people chose to only talk about Close-up photos of me Taken with a long lens camera By a press photographer that Would distort anyone's face!!"

She noted that she'll always be unapologetically herself, no matter what others think.

"Once again I am caught in the glare of ageism and misogyny that permeates the world we live in," she continued. "A world that refuses to celebrate women past the age of 45 and feels the need to punish her if she continues to be strong-willed, hard-working and adventurous. I have never apologized for any of the creative choices I have made nor the way that I look or dress and I'm not going to start."

On that note, take a look at Madonna's fierce shag haircut, plus, all of the other celebs marching to the beat of their own drum with epic makeovers.

The "Say So" singer showed off her dramatic hair transformation on Instagram, debuting bright purple hair and a spooky spider design on the back of her head.

The Kick-Ass actress debuted a fresh bob haircut, which she hasn't rocked in quite some time.

The American Idol judge revived her signature style of 2008 and revealed baby bangs in a June 20 Instagram.

The Vampire Diaries actress debuted fringe bangs for the Los Angeles premiere of her new film Out-Laws in June.

The "Vogue" singer debuted an edgy shag haircut on June 11.

The Dance Moms alum proved you can be blonde and brunette at the same time with her recent hair change.

The High School Musical alum has entered her French girl era, after showing off her new curtain bangs.

The New Girl alum ditched her trademark brown hair and blunt bangs for a sky-high blonde 'do for her upcoming appearance on the '80s-based Apple TV+ series Physical.

The "Over It" artist headed into summer with a shorter cut and new hair color, debuting her blonde bob to Instagram in May 2023.

The X-Men star kissed her shoulder-length hair goodbye and debuted a pixie cut on May 26.

While attending the Louis Vuitton cruise show in Italy on May 24, Emma debuted curtain bangs—a style she often rocked in the mid-2010s.

The Sweet Home Alabama actress debuted wispy fringe bangs in a stunning selfie. 

The Poosh founder went back to her brunette roots, debuting a new look. As she put it on Instagram, she's a "brunette4lyfe."

Amid her ongoing transformation journey, the Rob & Chyna alum debuted a short pixie cut with shaved sides.

On May 15, the pop star opted for a bold hair color, rocking jet-black hair.

Helen Mirren wowed at the 2023 Cannes Film Festival, as she debuted vibrant blue hair.

Playing Lily Bloom in the film adaptation of Colleen Hoover's It Ends With Us, the actress was seen with red hair while filming scenes in New York City on May 15, 2023.

The Star Wars actress debuted her newly shaved head on May 10, writing on Instagram, "Happy without hair!"

On April 24, the Tangled actress debuted a fresh cut and fringe bangs.

The "Flowers" singer unveiled a drastic hair change, going back to her brunette roots, at The Daily Front Row's Seventh Annual Fashion Los Angeles Awards.

The TikTok star debuted a drastic hair change at Coachella 2023, unveiling a blonde bob look.

Ava Phillippe, the daughter of Reese Witherspoon and Ryan Phillippe, debuted blunt bangs in an April 4 Instagram.

The Elvis star went bald for his role as Feyd-Rautha in Dune: Part Two.

The actress debuted a long bob on April 3 that's perfect for spring.

"@craphairclub hair is giving me so much joy still," the daughter of Nicole Kidman and Tom Cruise shared on Instagram March 29 along with a photo of her 'do. "Thank you."

The Pretty Woman star showed off her fringe bangs and fresh hair color on March 27.

The supermodel debuted a pixie haircut in a March 20 Instagram, while also sharing behind-the-scenes snapshots of her photoshoot with Pop magazine.

The star debuted a red hot new 'do in March 2023.

Kourtney debuted her biggest hair transformation in March 2023.

After reverting back from blonde to brunette, the SKIMS founder zhuzhed up her signature look with curtain bangs.