Venus and Serena Williams’ Best Y2K Beauty Looks Are a Grand Slam

Beauty We just can’t enough of their beaded braids. by Jacquelyn Greenfield November 19, 2021

Before they were Olympic medalists, before they won multiple Grand Slam titles, and before they were the athletic and business powerhouses that they are today, Venus & Serena Williams were just a couple of teens playing tennis and honing their craft. Now, as we gear up to watch King Richard , the 1990s biopic depicting the sisters and their father and first coach, Richard Williams as he pushed them towards superstardom, we can take a look back at another part of their evolution. We would be remiss not to mention that the sisters have also made an indelible mark on fashion and beauty. Tap through to see Venus and Serena’s best ’90s and early ’00s beauty moments, on and off the court.

Fiona Hanson - PA Images/PA Images/Getty Images 1992, Centre Court Before making her debut at Centre Court with her sister, Venus wore her micro braids with green and white beads while Serena wore all (tennis) white beads.

Franck Seguin/Corbis Sport/Getty Images 1998, French Open At the French Open back in 1998, both sisters–now with braces–wore their hair in matching white, blue, and aqua beads. Serena added bright blue flower clips to her hair.

Yves Forestier/Sygma/Getty Images 1999, ROLAND GARROS French Open Playing with one another at the 1999 French Open, the Williams sisters wore their hair in feed-in braids– white and yellow beads for Serena and all white beads for Venus.

Bernie Nunez/Getty Images Sport/Getty Images 1999, US Open Later that year, the sisters played in the US Open and wore their hair braided back with all white beads. Serena added a pop of color with just two strands of pink in the back.

Art SEITZ/Gamma-Rapho/Getty Images 2000, F.A.O. Schwartz Embracing early stardom, Serena and Venus wore their hair in micro braids without beads for the launch of their very own dolls.

Jim Smeal/Ron Galella Collection/Getty Images 2000, Teen Choice Awards The sisters went for matching pink ensembles and brown lipstick for the 2000 Teen Choice Awards.

Pool BENAINOUS/SCORCELLETTI/Gamma-Rapho/Getty Images 2000, Laureus Sports Awards Arriving at the Laureus Sports Awards in Monaco, Serena wore her braids with curly Y2K trendrils and a shiny red lip, while Venus wore frosty pink eyeshadow to match her outfit.

Carmen Valdes/Ron Galella Collection/Getty Images 2001, Essence Awards At the 2001 Essence Awards, the sisters both wore a swipe of brown gloss and shimmery eye shadow. However, Serena opted for blonde Fulani braids while Venus stuck with her chocolate brown hair in micro braids.

Jeff Kravitz/FilmMagic/Getty Images 2002, VH1 Vogue Fashion Awards With a full change up for the VH1 Vogue Fashion Awards, Serena opted for curly blonde micro links while Venus gave us a collar length nearly-black bob with deep side bangs.

Evan Agostini/Getty Images Entertainment/Getty Images 2003, MTV Video Music Awards For the 2003 VMAs, Venus wore her hair slicked back in a side ponytail with darkly-lined lips and Serena wore her hair in brown and blonde curls with silvery eyeshadow and a touch of blush.

Carley Margolis/FilmMagic/Getty Images 2004, WTA Glam Slam New York City Here, the Williams sisters kept their makeup very minimal with a touch of gloss and black eyeliner. Serena tried out highlighted hair, while Venus kept up her rich black color.

Jon Kopaloff/Getty Images Entertainment/Getty Images 2021, King Richard Premiere Fast forward to 2021, the Williams sisters stunned on the red carpet for the premiere of the biopic, King Richard . While their style has changed and become more glamorous over the years, Venus threw it back to their early days in the spotlight by wearing silver and translucent beads with an impressive braided ponytail.

More from NYLON

Florence Pugh’s Beauty Evolution, From Breakout Ingenue to Marvel Superstar By Jacquelyn Greenfield Dua Lipa’s Best Red Carpet Beauty Moments By Jacquelyn Greenfield