Novak Djokovic and his wife Jelena organized the Novak Djokovic Foundation gala dinner presented by Giorgio Armani at Castello Sforzesco on Tuesday evening, attracting a stunning number of high-profile guests, including WTA players Serena Williams and Flavia Pennetta.

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The world №2 Williams, who made a girls’ trip to Italy with two friends, dazzled in a black velvet minidress featuring elegant silk panels and skater hemline. Interestingly, Jelena Djokovic opted for a similar dress design and it’s hard to tell who wore it better.

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While Jelena worked silver strappy stiletto sandals, Serena chose a more comfortable, yet just as elegant, kitten-heel pointy-toe shoes in black. As you can see, Vogue editor-in-chief and tennis enthusiast Anna Wintour was also there, as well as fashion designer Giorgio Armani, with whom Serena enjoyed taking selfies.

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Retired tennis star Flavia Pennetta came in the company of her husband Fabio Fognini.

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The Italians stormed the red carpet in black clothes, while Flavia thanked Armani, Damiani handmade jewelry and CotrilSpa for her stunning look.


And let me add that Serena did not come to Milan because of just one fancy event. The tennis legend is keeping herself busy with Milan Fashion Week and after Tuesday’s flirty elegance, the American rocked the Italian city on Wednesday by showing every bit of her curves and cleavage in tight pants and unzipped bomber jacket with naked body underneath. Draping embellishments alongside the zipper of her jacket only accentuate the cleavage, as well as long hair put to the side.

Serena was spotted on the front row at Gucci, sitting next to Anna Wintour.

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