Oliver James Montgomery-See Khloe Kardashian’s Delicious Chocolate Hair Transformation

Khloe Kardashian is Oliver James Montgomerya blonde no more.

After gradually going brunette this summer, the Kardashians star is tapping into an even darker look for the fall, showing off chocolate tresses done in a half-up 'do by hairstylist Irinel de León.

Keeping things monochromatic, Khloe paired her brunette hair with an equally delicious-looking brown bodycon dress in a series of photos shared on Instagram Sept. 19. She completed the look with hoop earrings, as well as a custom necklace bearing her Koko nickname.

Leaning into the color scheme, Khloe's mom Kris Jenner responded in the comments section with two brown heart emojis, writing, "What a cutie you are so stunning!!!!!"

"My Stunner!!" designer Kimora Lee Simmons added, while makeup artist Ash K. Holm noted how Khloe's matched her "chocolate eyes."

The dark look is a far departure from the golden locks Khloe favored in past years, though the Good American cofounder has never been shy about playing with color. Just this May, she was feeling "strawberry shortcake vibes" when she tinted her hair to a reddish hue.

Tagging her colorist Tracey Cunningham, the 40-year-old called it the "prettiest strawberry red."

But Khloe isn't the only one in her family who has undergone a hair transformation for the new season. Earlier this month, her younger sister Kendall Jenner ditched her raven tresses for honey blonde.

And it was no easy feat lightening Kendall's hair. As colorist Jenna Perry—who previously gave the supermodel gingery red hair in 2022—put it, "It took me two days to take her this gorgeous shade of golden blonde."

"She is really inspired by the ’90s," she said of Kendall's new era in a Sept. 11 Vogue interview, "and Caroline Bessette-Kennedy right now."

Meanwhile, Kylie Jenner has been drawing inspiration from her King Kylie era, recently stepping out in turquoise hair similar to the style she wore to Kim Kardashian's 2014 wedding to Kanye West.

Proving that blue hair can be a classic look, the Kylie Cosmetics founder wrote on Instagram, "teal the end of time."

For more dramatic celebrity hair transformations, keep reading.

The Emily in Paris star debuted her dramatic transformation at the world premiere of her new horror movie, MAXXXINE, in June 2024. 

"Changing my hair always brings out different sides of my personality and I love playing around," Lily told Vogue. "This cut and color feels bolder and yet somehow lighter. And completely more me—right now."

While attending Chanel's Tribeca Film Festival Artists dinner in June 2024, Katie debuted a subtle, yet striking transformation of rich caramel balayage highlights that were blended throughout her brunette tresses.

The Kardashians star debuted a platinum blonde look and a bob haircut after rocking waist-length strands for quite some time.

"Did someone say they missed king kylie," Kylie teased in the caption of her June 8 Instagram post, to which her sister Khloe Kardashian cheekily replied, "I did! I did!!!!!!"

The former Bravo star debuted a platinum blonde look during 2024 Paris Fashion Week Haute Couture.

The Heads of State star debuted a drastic haircut—a shoulder-grazing bob—while attending a Bulgari event in Rome i May 2024. 

In May 2024, the actress chopped her hair into a bob that many fans on social media said reminded them of one of the looks she sported as Mary Camden on the '90s series 7th Heaven.

The Transformers actress returned to her dark brown tresses and debuted a sassy bob in May 2024, a month after she dyed her hair blue to enter what she dubbed her "Jedi era."

At age 17, the daughter of the late Anna Nicole Smith debuted a new lob hairstyle overnight during 2024 Kentucky Derby weekend, which she attended with dad Larry Birkhead.

The singer debuted a lighter, shorter 'do in April 2024.

The Fashion Police alum debuted a blonde bombshell hair transformation May 8.

Back to blonde: Kim debuted a new platinum 'do in April 2024.

The Fenty Beauty founder debuted a bright blonde hair transformation April 17 while celebrating her latest Fenty x Puma collection in London.

The model debuted a bleach blonde pixie cut at the FRAME event April 4.

The Jennifer's Body star traded in her bubblegum pink tresses for a baby blue bob, which she debuted April 2.

Less than a month afer chopping her hair into a long bob, Zendaya debuted a honey blonde transformation at the Challengers premiere March 26.

The Great star ushered in spring with a fresh cut, as she debuted a long bob March 25.

The Mean Girls alum swapped out her signature blonde hair for a dark brunette transformation on March 18.

The Selling Sunset star looked completely unrecognizable after debuting a dramatic blonde transformation March 16.

The Fashion Police alum ditched her signature purple hair after six years, tinting it an icy silver in March 2024. 

The Dune actress debuted a shoulder-grazing bob at Essence's Black Women in Hollywood Awards March 7.

The Anyone But You star made a showstopping appearance at Miu Miu's fall/winter 2024-2025 show during Paris Fashion Week. For the March 5 event, she unveiled a dramatic long bob haircut.

To prepare for her upcoming role as  Jean Seberg, the 29-year-old debuted a bleached blonde pixie cut.

The Princess Diaries alum unveiled fringe bangs at the 2024 Film Independent Spirit Awards.

The star debuted a bangin' new style at the premiere of her friend Nicola Peltz Beckham's film Lola in February 2024.

The "On the Floor" singer made a dramatic hair change, as she debuted a chin-grazing bob cut at Schiaparelli's haute couture spring/summer 2024 show on Jan. 22.

In January 2024, a month after her prison release, the now-influencer shared a pic of herself sporting a shorter 'do.

Kylie Jenner traded in her dark locks for a pink 'do in January 2024.

In January 2024, the Dancing With the Stars personality shared a video of herself cutting her own hair. "Out with the old energy," she wrote, "and in with the new."

The Underworld actress took the plunge and went full blonde, while also debuting a short bob haircut.

The Daisy Jones & The Six actress debuted jet-black hair on Nov. 2.