Since attending her first show in 1999, she's sat on the front row at many more Fashion Week presentations, became an ambassador for the house in 2018, and even hosted the Met Gala 2023, where the event's annual theme was centred on the late designer and former Chanel Creative Director Karl Lagerfeld.
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It was unsurprising therefore that she stepped out in a look from the luxury French label for the premiere of Ferrari - her latest movie - at Odeon Luxe Leicester Square on Monday, and it was a masterclass in elevated eveningwear florals.
Though the 2023 Fashion Awards were on the same evening, Penelope brought her own award-worthy glamour to London in a white chiffon gown complete with ethereal tiered material and statement camellias in pink and grey hues. The dress boasted a sequined black bustier to give the floral dress a touch of evening glamour.
Taking the ensemble from uber-feminine to sophisticated formal, the look - which was from the label's Spring/Summer Haute Couture 2022 collection - was complete with an ultra-cropped black tailored jacket to give it a more structured and elevated feel.
Granted, Chanel's traffic-stopping shows are hotly anticipated every season, but this particular presentation became a social media sensation after Charlotte Casiraghi - the daughter of Princess Caroline of Hanover and granddaughter of Grace Kelly, who is also a Chanel brand ambassador - opened the show riding a horse wearing a dazzling tweed riding jacket.
“I've been with [Chanel] always. I see the same people here… Some of them I met in 1999," Penelope recently told Vogue, “I know so many of them—seamstresses and people that work in every department, and everyone feels very grateful to be part of it.”
She accompanied her striking dress from the art-inspired collection with a voluminous middle-parting updo and a tightly curled ponytail.
If you want to eschew sparkles and feathers this party season, elevate a floral frock with a crisply tailored blazer like Penelope and you're good to go.