In ‘Great Outfits in Fashion History,’ Fashionista editors are reminiscing about their all-time favorite looks – those celebrity style moments that truly leave a lasting impression and inspire attempts at home recreations.

Over the years, Venus and Serena Williams have been a wellspring of fashion inspiration, both on and off the court. They’ve cultivated enduring relationships with premier luxury houses, frequented front rows at fashion weeks, and even launched their own fashion labels (EleVen by Venus Williams and S by Serena, respectively). Each sister has her distinct aesthetic and style preferences, always allowing their individuality to shine through – even when they opt for coordinated looks on the red carpet.

One particularly memorable moment of matching sibling style occurred at the 2000 Teen Choice Awards, where the duo each claimed surfboards in the “Choice Female Athletes” category. Venus opted for a strapless, sequined corset-style top paired with low-rise, matte leather-look flared pants (accentuated with a silver chain belt, a quintessential touch of the early 2000s) and heeled sandals, all in a vibrant shade of pink. Serena embraced the same color palette, albeit in a softer pastel hue, donning a strapless mini dress adorned with an embroidered flower detail at the hip and featuring a subtle asymmetric hemline. Both sisters accessorized their ensembles with sparkling silver choker necklaces, adding a touch of glamour to their coordinated looks.