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The daughter of Prince and Princess Michael of Kent, 45, greeted Catherine, 44, alongside other senior members of the royals, including King Charles and Queen Camilla, on the second day of the racing event.
Gabriella, who looked elegant in a £1,395 sky blue Claire Mischevani coat dress - and in true Ascot fashion - a chic, wide-brimmed hat - is a regular attendee of the Berkshire-based racing event, and in 2024, Royal Ascot marked her first public appearance following the loss of her husband.
Financier Thomas had been found dead with a 'traumatic head wound' and a gun near his body in an outbuilding of his parents' Cotswolds home on February 25 at the age of 45.
In a statement released by Buckingham Palace shortly after Mr Kingston's death, Lady Gabriella described him as an 'exceptional man who lit up the lives of all who knew him'.
Following his death, the Princess of Wales showed her support to Gabriella by reaching out to her for help in planning her carol concert.
Lady Gabriella was said to be a 'real member of the carol service team' and influential in choosing the musical performances.
As a singer-songwriter who has previously released a charity single, she brought her expertise to the concert.
Lady Gabriella, dressed in a sky blue coat dress and white hat, was spotted having a warm catch up with the Princess of Wales
Gabriella attended day two of Royal Ascot at Ascot Racecourse in Berkshire on Wednesday
An insider said she 'enjoyed her role within the service and was excited to be a part of it', while the Princess was 'incredibly grateful for her contribution'.
A friend added: 'She was very touched and grateful to the Princess to be asked to contribute to her very special concert. She felt honoured.'
One of Lady Gabriella's personal touches was helping to engage youth charity Restore the Music, which played as guests queued to enter the service.
Polly Moore, CEO of Restore the Music, said: 'Lady Gabriella is incredibly passionate about music and helping young people find their voice.
'She has been an ambassador for us for the past five years and often attends our events.
'When she messaged to ask if I would be interested, I said, 'Are you kidding, of course!'
'She was incredibly approachable and a brilliant sounding board in the planning process. She's the most wonderful person. I'm extremely grateful to her.'
In one sweet moment from today, Gabriella, who completed her ensemble with a pair of suede, nude heels, an Aspinall of London bag and white flower-shaped earrings, was spotted warmly chatting to Catherine, after greeting other members on the racecourse's green lawn.
The 45-year-old beamed as she chatted to attendees on the Berkshire-based racecourse's lawn
Meanwhile, the Princess of Wales brought the sunshine to Royal Ascot after a two-year absence as she arrived at the races wearing a bright yellow dress today.
Catherine, 44, joined the family's carriage procession alongside her husband, the Prince of Wales, as they travelled behind the King and Queen today.
The future Queen's canary yellow outfit is from the label Roksanda, and Catherine paired it with a matching hat, while Prince William pinned yellow flowers to his lapel to complement his wife's ensemble.
This is the third time Catherine has donned the frock, having previously worn it on a State Visit to Jamaica and at the Wimbledon championships in 2022.
Her mother, Carole Middleton, also repurposed the dress she wore to Pippa Middleton's wedding nine years ago as she arrived at Ascot alongside her daughter-in-law, Alizee Thevenet.
Racegoers were delighted to see the Princess riding in the second royal carriage alongside Prince William, 43, after she was forced to skip the event in 2025 while trying to 'find the right balance' after her cancer treatment.
They were accompanied by the Duke and Duchess of Richmond and Gordon, riding behind King Charles and Queen Camilla in the first carriage.
The last time Catherine attended Ascot was in 2023, when the future Queen famously wore a 'tomato red' Alexander McQueen dress - proving Kate is always one step ahead of fashion trends.
Gabriella looked elegant in a £1,395 sky blue Claire Mischevani coat dress
The fiery hue of Kate's frock is Ascot's inaugural colour of the year, as the official lookbook reads: 'Bright tomato is the kind of colour that doesn't just join the party at Royal Ascot - it leads it.'
Catherine looked elated to be back in the Windsor Enclosure, enjoying the company of other royals, including Lady Sarah Chatto and her husband Daniel Chatto, as well as her mother, Carole Middleton.
Carole, 71, cut a stylish figure as she donned a pink coat dress that she first wore to her younger daughter, Pippa Middleton's wedding on May 20, 2017.
The Middleton matriarch appeared to be ageing backwards as she repurposed the blush pink Catherine Walker ensemble for a day out at the races in Berkshire.
She paired the designer dress with a matching hat and shoes, both from Emmy London, as Carole happily posed for pictures alongside Alizee.
As Royal Ascot, which will run until June 20, gets underway, the royals in attendance on day one included the King and Queen, Mike and Zara Tindall, as well as Princess Anne.
But all eyes were on Harriet Sperling yesterday as she made her official debut as a member of the Royal Family following her 'intimate' Cotswolds wedding to Peter Phillips less than two weeks ago.
The new Mrs Peter Phillips joined the traditional carriage procession as she arrived at the racecourse in the second landau alongside her husband and mother-in-law, the Princess Royal.
Royal Ascot, the jewel in the crown of the UK racing calendar, started yesterday with the Queen Anne Stakes and the King Charles III Stakes, and will run until Saturday.
The prestigious festival is just as famous for its fashion as it is for its races - and this year, statement hats were the focal point of revellers' eye-popping looks as day one of the annual race meeting got underway.
Dressed to impress, guests wore a variety of show-stopping headpieces as they descended on Ascot for a day of equestrian fun.
The festival was founded by Queen Anne in 1711 after she declared Ascot ideal for 'horses fit for kings' and has today become a major social event as well as a sporting attraction.
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