Tennis icons Venus and Serena Williams, just about 15 months apart in age, have been known as a famous duo since breaking into the professional athletic world as teenage phenoms in the 1990s. While each sister has amassed a list of accomplishments in women’s singles tennis and faced one another many times from across the net, they have a long history as doubles partners as well, with 22 career titles under their belts as a duo.

The two have been by each other’s sides through many life chapters, from winning trophies to serving as maid of honor at each other’s weddings — and they’ll be side by side yet again on Monday evening at the Cincinnati Open, reuniting for doubles for the first time since 2022. Ahead of the match up, WWD/FN rounds up some of their on and off-court looks through the years.

In 1999, Venus was a Reebok partner while Serena was a Puma athlete, which was reflected through their looks at the time. The two faced each other in the Lipton Championships, now the Miami Open, with Venus ultimately winning the final match. They were both embracing color on this occasion, with a red Reebok top for Venus and a kit with yellow accents for Serena; their relatively chunky sneakers featured these color accents as well.

Serena and Venus attended the 2000 Teen Choice Awards in coordinated pink looks embodying Y2K glamour. Serena opted for a strapless minidress with an asymmetric hemline while Venus opted for flared pants and a strapless top with a disco ball-esque design. Both opted for strappy sandals, with Serena going for a sparkling embellished pair and Venus donning a style in a hue which matched her two-piece ensemble.

White looks for Wimbledon: the Williams sisters followed the London tennis tournament’s famous dress code with respective kits from Venus’ own brand EleVen by Venus Williams and Nike. Venus’ shoes looked like a court style from her affordable shoe lineup by EleVen and Steve & Barry’s, which launched in 2007, while Serena laced up a Nike set featuring gold accents including the Swoosh. She signed with the athletic brand in 2003.

It was a complementary colorful moment for Venus and Serena on day eleven of the 2013 US Open. Venus had on a vivid floral top from her EleVen brand with a pink pleated skirt and Nike sneakers. Meanwhile, Serena repped Nike from head-to-toe but still aligned with her sister’s palette with a peach-hued headband, gray sleeveless top, dusty rose skirt and player exclusive peach and gray Nike Lunar Mirabella sneakers.

The sisters both wore on-theme green, but with opposite footwear choices, for the launch party for Serena’s Wyn Beauty brand in 2024. The founder opted for a one-shoulder knee-length dress with Nike sneakers while Venus wore silver sandals with a darker green dress featuring gradient trim and an undulating asymmetric hemline.

It was a family affair at the Gucci men’s spring 2025 show in Milan, which Venus and Serena attended with their mother Oracene Price and sister Lyndrea Price. Venus and Serena showcased complementary warm hues, with the elder sister wearing a burgundy leather jacket over white pieces and the younger sister wearing a monochrome blush pink suit look. Venus completed her look with glossy burgundy Gucci Signora slingback pumps while Serena modeled a pair of clear sandals with a beige base.