Serena Williams may be known for her tennis chops, but her historic career in the sport has also been marked by countless hair and makeup styles. The athlete hasn’t shied away from experimenting with different looks through the years, trying out trends like baby highlights and graphic eyeliner.

Below, see Williams’ best beauty moments from the ’90s to today.

1999

Serena Williams at the Evert Cup in 1999. AFP VIA GETTY IMAGES

In their youth, Venus and Serena were known for wearing beaded braids. At the Evert Cup in 1999, Serena defeated Germany’s Steffi Graf in the final while wearing rows of colorful heart-shaped beads in her hair.

2000

Serena Williams at the 2000 Teen Choice Awards. FILMMAGIC, INC

Williams’ makeup at the 2000 Teen Choice Awards was peak Y2K: the star athlete paired glittery purple eyeshadow with an iridescent lip, as well as baby blond highlights.

2004

Serena Williams at the premiere of “Friday Night Lights.” FILMMAGIC

Williams attended the premiere of “Friday Night Lights” in 2004 wearing a brown smoky eye with winged liner. She also added a pop of rosy blush and a glossy red ombré lip.

2017

Serena Williams at Glamour’s 2017 Women of the Year party. GETTY IMAGES

At Glamour’s 2017 Women of the Year party, Williams went full vamp, wearing a dark wine-colored lip and a voluminous braid adorned with gold accessories.

2020

Serena Williams at the 2020 Australian Open. GETTY IMAGES

For the 2020 Australian Open, Williams sported a colorful bedazzled manicure featuring one of the country’s native critters: a koala.

2021

Serena Williams attends the 2021 LACMA Art + Film Gala. WIREIMAGE

Williams embraced fuchsia hues at the 2021 LACMA Art + Film, wearing pops of color on her lips and eyelids.

2022

Serena Williams at the U.S. Open in 2022. GETTY IMAGES

For her final professional tennis match at the 2022 U.S. Open, Williams wore rhinestones in her hair, coordinating with her crystal-encrusted Nike ensemble.

2022

Serena Williams attends Balmain’s fall 2022 fashion show. CORBIS VIA GETTY IMAGES

While attending Balmain’s fall 2022 fashion show, Williams wore winged eyeliner that extended across her waterline, adding on a deep mauve lip and matching blush.

2023

Serena Williams at the 2023 Met Gala. AFP VIA GETTY IMAGES

At the Met Gala celebrating Chanel’s late creative director, Karl Lagerfeld, Williams wore one of the brand’s iconic motifs, pearls, in the form of a layered headband. Meanwhile, her makeup consisted of graphic winged eyeliner, a red lip and matching blush.

2023

Serena Williams at the 2023 CFDA Awards. GETTY IMAGES

To receive the Fashion Icon award at the 2023 CFDA Awards, Thom Browne created a custom sequined gown for Williams, which she accessorized with the designer’s trademark red, white and navy ribbon, wrapping it around the braid in her hair.