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Then And Now… The Met Gala

By Mark Winters

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Thanks to an appreciation inspired by my mother Virginia, who spent her career working in the industry, I have long been interested in fashion.

This year’s Metropolitan Museum of Art’s Costume Institute Gala in New York on May 4th was compelling because tennis players I had seen early in their careers before they became elite competitors attended.

Venus and Serena Williams, along with Naomi Osaka, were as riveting as their games wearing “Haute Couture” originals.

I first watched the sisters in 1990 with tennis legend Jack Kramer at the Los Angeles Tennis Club when they were “Youth versus Experience” participants, the annual event held in late May at the storied facility. Kramer, a superlative judge of playing ability, told me that Venus would be very good, but added, “Serena will be better…”

Serena and Venus Williams, LA84 Foundation/NJTL. Photo: Cynthia Lum

That summer they took part in the LA84 Foundation/NJTL “Between Match Activity” at the Volvo Tennis Los Angeles men’s tournament. It is almost incidental mentioning that Stefan Edberg defeated Michael Chang 7-6, 2-6, 7-6 in the singles final and Scott Davis and David Pate won the doubles 3-6, 6-1, 6-3 over Peter Lundgren and Paul Wekesa… because Venus and Serena had people talking.

Twenty-eight years later in 2018, having heard about her “throw caution to the wind ball striking flair”, I went to Indian Wells to see Naomi Osaka for the first time… and the 20-year-old ranked No. 44 didn’t disappoint. She decimated the field, downing Maria Sharapova, Agnieszka Radwańska, Karolína Plíšková, along with World No. 1 Simona Halep. In the final she won her first WTA title, dispatching  Daria Kasatkina 6-3, 6-2.

Naomi Osaka in the all-red reveal at this year’s Met Gala. Photo: Instagram

Her amazing season continued… Seeded No. 20, she surprised No. 17 Serena Williams, 6-2, 6-4 in the clamorous 2018 US Open final.

Individually they were mesmerizing… and it was more than their height – Venus was 6’ 1”, Serena though listed at 5’9” seemed taller, and Naomi was 5’11”…

But from an early age there was more. The way they carried themselves was defining… moving to their games, lanky Venus seemed to float covering the entire court in a step or two; Serena “took no prisoners …” using an unbridled aggression to dominate; and Naomi regularly instilled shots with “Where did that come from…” magic.

Being more accurate – They had presence.

The Williams were always stylish wearing beads in their hair when they began playing the tour. Venus, ever fashion conscious even with her first clothing contracts, used patterns and color combinations to “Dress Out…”. In time she moved to EleVen, her own brand that featured can-can and flapper presentations – before segueing to high fashion ensembles highlighting navy and black. At this year’s Miami Open, she platformed a mirrored leather jacket.

Venus Williams wearing a Swarovski crystal mesh gown. Photo: Swarovski

Over time, Serena “Wear…” featured a denim skirt and demi-boots; a Flo-Jo pink and black one legged outfit; there were figure skating and ballerina ensembles; she debuted a trenchcoat and colorful panties look at The Championships… and who can forget the 2002 US Open’s Eartha Kitt inspired “Catsuit…” and the updated version that impressionnée at Roland-Garros in 2018.

Osaka has been fascinating combining her shyness cleverly with her Haitian/Japanese cultural identity, most recently using Harajuku-inspired bold cuts and color schemes.

Often she has made statements, such as the seven masks she designed with the names of victims of racial violence, and wore on her way to winning the 2020 US Open.

WLM Tennis has posted stories I have written about the latest hues and patterns annually unveiled, almost like fashion industry’s runway shows, at Melbourne, Paris and New York. Osaka has turned the majors into “can’t wait to see what she will wear…” extravaganzas.

At the 2026 Australian Open she enthralled walking on court wearing an elegant, veiled wide-brim white hat then played in a jellyfish green and teal dress.

After the Met Gala began in 1948, it quickly became a “Must…” attend activity. “Costume Art” was this year’s theme and Beyoncé, Nicole Kidman, and Venus Williams were the co-chairs. Those appearing on the red carpet followed the “Fashion is Art” dress code …as brought out by sightings of Angela Bassett, Bad Bunny, Heidi Klum, Madonna, Rihanna, along with Anne Hathaway, Emily Blunt, and Stanley Tucci, who were original The Devil Wears Prada cast members.

The “Tennis Fashionistas” were spectacular. Venus wore a one-off black mesh crystal Swarovski couture gown designed by Giovanna Engelbert and an equally eye catching necklace.

Serena Williams dressed for the Met Gala by Marc Jacobs. Photo: Met Gala

Serena was in a metallic silver gown with a thigh-high slit by Marc Jacobs and attention grabbing golden gladiator heels.

Naomi, who was attending the event for the first time in five years, relied on Robert Wun’s imagination. Having designed her AO two-part look, he used the successful formula to create a shedding image that allowed her, to transform from a sculptured white hat and coat into a red crystallized gown that represented human anatomy. 

Most important, the affair realized a record $42 million dollars for Metropolitan Museum of Art’s Costume Institute breaking the $31 million standard set last year.

And, not to be outdone, the “Tennis Fashionistas” again proved that no matter the venue, they will command attention…

Title photo of Naomi Osaka in her hat and coat for the Met Gala via Robert Wun

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