EXCLUSIVE: Secrets of Princess Kate's Sister Pippa Middleton's Massive Engagement Ring Bling — Now Valued at Nearly $300,000
Pippa Middleton has one impressive rock on her finger.
Dec. 19 2025, Published 7:05 p.m. ET
Pippa Middleton has long resisted living in her sister's shadow, but the scale and craftsmanship of her engagement ring from James Matthews have ensured it still commands attention in its own right.
RadarOnline.com can reveal experts now value the Art Deco-inspired jewel at close to $300,000.
A 'Classic, Enduring Design'
Despite comparisons to Kate Middleton, Pippa’s Art Deco ring has stood out for its modern elegance.
The ring entered public view after Middleton, 42, the younger sister of Catherine, Princess of Wales, 43, announced her engagement to Matthews, 50, in July 2016.
The couple confirmed the proposal on July 17 after Matthews asked the question during a trip to England's Lake District. At the center of the ring is a 3-carat Asscher-cut diamond, a style rooted in the bold symmetry of the 1920s.
The stone is framed by an octagonal halo of channel-set diamonds, blending antique references with contemporary precision.
A jewelry industry source said: "It's a classic, enduring design that won't date and will look just as elegant decades from now as it does today."
The Royal Connection in the Cut
James Matthews proposed to Pippa during a trip to England’s Lake District.
The Asscher name carries a subtle royal resonance.
The cut was developed by Joseph Asscher, whose Royal Asscher Diamond Company worked extensively with European royalty, including cutting pieces from the famous Cullinan diamond for the British Crown.
While the couple has never confirmed the designer, the ring is widely believed to have been commissioned from Robinson Pelham, a favored jeweler of the Middleton family.
One appraiser noted: "Asscher-cut diamonds require exceptional clarity to achieve a perfect cut. If the stone is flawless, it could be worth around $263,000 or easily near $300,000 due to its provenance."
Where Was Pippa Middleton?
Pippa Middleton described sharing a competitive and adventurous spirit with Matthews
Middleton has been photographed wearing the set at major events, including the 2023 coronation.
However, she was notably absent from her siblings' festive Together At Christmas service on December 5, 2025, for the first time in years.
While the rest of the Middleton clan – parents Carole and Michael, and brother James – were in attendance at Westminster Abbey, Pippa was spotted thousands of miles away.
Sources confirmed she was traveling in the Middle East, where she and her husband were seen at the Abu Dhabi Grand Prix just two days later.
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A Feud Brewing?
The engagement ring remained one of the most talked-about non-royal jewels.
Insiders were quick to dismiss rumors of a rift between the sisters.
"It wasn't a snub," a source clarified. "Pippa has been increasingly busy with international commitments. Attending the Grand Prix with James, who is on the board of Williams Racing, simply coincided with the carol concert."
Her only other absence from the service was in 2021, which was attributed to limited capacity during the pandemic.
For the 2025 holiday season, it appears the younger Middleton sister is prioritizing a more "globally focused" schedule.
