5 Times Pippa Middleton's Jewelry Meant More Than You Realized

While Catherine, Princess of Wales, turns heads with her wonderful sense of style, her sister Pippa Middleton has perhaps an even more notable (and expensive) wardrobe. From stealing the spotlight at her sister's wedding as "her royal hotness," Pippa's had a beautiful style transformation over the years. She's no stranger to wearing extravagant accessories, like a £14,500 Cartier watch (almost $18,000 in 2025) housing 50 brilliant-cut diamonds, and wears jewelry that celebrities like Rihanna and Kristen Stewart also enjoy.

Speaking with People, jeweler Annoushka Ducas described Pippa's style as "modern, easy, effortless, it's not very contrived and it's very easy to relate to." Her style can also be sentimental, as evidenced by the jewelry she's worn over the years. From her beautiful wedding accessories to a gift for her sister, Pippa Middleton's jewelry has carried more meaning than you may have thought at first glance.

In 2017, Pippa Middleton married James Matthews, heir to the Scottish title of Laird of Glen Affric, in a lovely ceremony at St Mark's Church on the Englefield Estate. She wore a beautiful white dress, of course, and an elegant tiara as well. Though it was an understated piece, Pippa's tiara was still something of a surprise as it was an untraditional accessory. "Although Pippa isn't an official member of the Royal Family, she broke the historic tradition that only royal brides should wear a tiara, and chose a stunning yet understated piece," Steven Stone's creative director Maxwell Stone told Express. Custom made by fine jewelry designer Robinson Pelham, the tiara was meant to represent simplicity in romance, according to the company cofounders Zoe Benyon and Vanessa Chilton.

Speaking with Vogue, Benyon said the tiara was "all about balance. You do not want the dress and tiara to fight, so one has to take a back seat." Robinson Pelham isn't one to take a backseat, however, as Pippa's wedding wasn't the first notable wedding the jewelers created stunning pieces for. They were commissioned by Michael and Carole Middleton, Pippa and Kate's parents, to make earrings for the Princess of Wales' 2011 nuptials.

Not one to let a fine set of jewelry go to waste, Pippa Middleton wore the same earrings to her wedding as she did to her sister's Catherine's wedding in 2011, adhering to the "something old" wedding tradition. Part of the Robinson Pelham set their parents commissioned, the earrings featured a pear-cut diamond suspended from leaves. They harken to her sister's wedding earrings, which included an acorn and oak leaf, honoring the Middleton family coat of arms.

Pippa was Kate's maid of honor in 2011, and her sister's wedding was plenty of people's first exposure to her. Surprisingly dressed in white, Pippa wore a figure-hugging satin dress that she later joked "fitted a little too well" (via People). Pippa carried her sister's train as Kate entered Westminster Abbey, putting Pippa square in the spotlight. "As I have found out," Pippa said at an event in 2014, "recognition has its upside, its downside and — you may say — its backside."

James Matthews stuck with tradition when proposing to Pippa. According to the Daily Mail, he asked her father, Michael Middleton, for his blessing before proposing to Pippa. "James is a traditionalist and very much wanted to do things properly. That meant getting his future father in law's consent," a friend of the couple told the outlet. He proposed to Pippa atop a hill, and she quickly accepted.

Being a wealthy hedge fund manager, Matthews proposed with an exorbitant engagement ring with an estimated value of £250,000 (over $300,000 in 2025). The ring features an Asscher-cut three-carat diamond at the center surrounded on eight sides by smaller jewels that speaks to Pippa's taste for understated elegance. "It's hugely practical, because it's quite flat and it will be very easy for her to wear,"  Annoushka Ducas told People. "It's a very timeless piece that will look as good now as it will in 50 years time."

The Asscher-cut also links her back to royalty, albeit in a roundabout way. Invented by Joseph Asscher in 1902, it was the first patented cut for a diamond and is known for "elongated, rectangular facets arranged concentrically" and "clipped corners rather than sharp points," according to the Royal Asscher Diamond Company. Originally just the Asscher Diamond Company, the jewelers were given permission to rename themselves as "royal" in 1980 by Queen Juliana of the Netherlands. The company modified the cut in 2001, creating the Royal Asscher Cut, and only 75 people in the world can precisely cut a diamond into the Royal Asscher Cut.

Pippa Middleton paired her beautiful engagement ring with a simple wedding band that lets the engagement ring's diamond shine. In an untraditional move for the royals, she stood firm in her desire for James Matthews to wear a wedding band as well.

"Traditionally, men of the aristocracy and gentry – and those without title or land but with good judgment – do not wear jewellery, which includes wedding bands," etiquette expert William Hanson told the Daily Mail. "Wearing rings and the like was considered a tad suspect." Matthews went against the grain in abiding by Pippa's wish; not even his new father-in-law Michael Middleton wore a wedding ring.

Notably, Pippa's brother-in-law Prince William eschews wearing a wedding ring as well. "He's not one for jewellery. He's never worn any. He decided he didn't want to wear one now. It's all down to personal preference," a palace source told Mirror of William's reluctance to wear a wedding ring. The absence of wedding bands on royal men shows just how sweet Matthews' breaking of tradition is.

When Prince George was born, Pippa Middleton gave her sister, Catherine, Princess of Wales, a very subtle and sentimental gift to celebrate: a necklace. At first blush, the gold necklace has three seemingly simple charms, with one in the shape of a young child and another circular pendant with "George Alexander Louis," the prince's full name, engraved. The third is a sweet nod to Princess Diana – a heart with the letter "W" engraved. Diana, Prince William's mother and the mother-in-law Kate never got to meet, wore a similar necklace after William was born. The torc necklace Diana wore had a gold pendant attached with "William" written out.

"Family was one of the closest things to Diana's heart so it's no surprise that this shone through in her jewellery, featuring personalised pieces and meaningful charms," the Merci Maman website, the boutique jeweler Pippa bought the necklace from, explained (via Mirror). The necklace she wore bearing her son's name was a gift from her husband, then Prince Charles. "Pippa Middleton continued this family tradition," with her gift to Kate, Merci Maman wrote. The boutique's founder Beatrice de Montille was appreciative that Kate wore it, and called her, "easily the most inspirational woman of our generation, as she is very elegant, and comes across as so modest" (via the Daily Mail). She mentioned that Pippa is a regular at Merci Maman, making it all the sweeter that Pippa would gift Kate a necklace from a favorite shop she frequents.