The Most Expensive Outfits Pippa Middleton Has Ever Worn

The 2011 wedding between Prince William and her sister, Kate Middleton, was the moment Pippa Middleton became a player on the global fashion stage. The younger Middleton was the maid of honor, and she went viral on that day for her scene-stealing, form-fitting dress. Since then, all fashion-watching eyes have been on Pippa Middleton to witness the shocking outfits she's worn, the skin-baring looks, and the ones that prove she has a similar style to big sis Princess Catherine.

When she first hit the scene, Middleton could be seen in a variety of brands, including many high street labels that carry pieces under $100. But as her profile grew and her wealth — she married billionaire hedge-fund manager James Matthews in 2017 — Pippa Middleton's outfits have noticeably changed since Kate's wedding. The biggest difference? They've become more expensive, with Pippa donning some pretty pricy ensembles in the years since. Cha-ching!

This was the look that put Pippa Middleton on the proverbial map. As the maid of honor at her sister Kate Middleton's 2011 wedding, she wore Alexander McQueen by Sarah Burton (same as the bride). And suddenly everyone wanted to know who this fit beauty was. It was none other than the bride's younger sister, who immediately found herself thrust in the limelight, with each of her fashion choices dissected by onlookers, who also started noting the price tags on her pieces. How much was the famed McQueen she wore to the Cambridge's royal wedding? Roughly $3,100. The exact style became available to purchase after the nuptials on net-a-porter.com.

But that isn't the most expensive piece she's worn to a wedding (that wasn't her own). Back in 2017, just after returning home from their honeymoon, she and husband James Matthews were guests at a wedding in Stockholm, Sweden. For the event, Middleton carried an $850 Wilbur & Gussie Lily clutch and wore the Erdem Kenzie dress with a price tag of $3,400, according to Vogue. The floor-length, flowing silk voile confection looked stunning on the newlywed; you'd hope so at that price. Middleton has proven that she has a penchant for gorgeous wedding attire; she'll want to be sure she doesn't show up the bride.

Since 2021, Princess Catherine has hosted an annual carol service at Westminster Abbey, which features a theme, such as remembering those who have passed or those who need a reminder of the love and empathy necessary in our world. It also features musical performances, including the princess herself playing the piano. The event hosts roughly 1,600 guests and Pippa Middleton has always been among the notable attendees.

For the 2022 evening, Middleton's look clocked in at a cool $7,500, and that's only based on the coat and accessories that we can see. Who knows what her outfit underneath cost! The most expensive items were the Kiki McDonough diamond and amethyst earrings (cost: $4,600) and the Tiffany Elsa Peretti Diamond pendant ($1,400). Her maroon Italian wool Karen Millen coat clocked in at just over $500, and her knee-high Penelope Chilvers boots also carried a $500 price tag, as did her Emmy London Natasha clutch bag.

Pippa Middleton has had three royal christenings to attend for her two nephews, Princes George and Louie, and niece, Princess Charlotte. For the latter's event, held in July 2015 at the family's Sandringham Estate, Middleton wore a cream ensemble. The look was understated, but that didn't mean it was inexpensive. No, this look rang in just under $10,000. So what exactly brought the price tag of this look to nearly 10 grand? For starters, the Jane Taylor hat. Similar styles available today cost roughly $4,000. (Kate Middleton is also a fan of the brand.) 

Then there's another pair of Kiki McDonough drop earrings–this time in lemon quartz. A similar pair costs $2,000. And how about the Emilia Wickstead dress? Though this exact dress is no longer available, a similar style will cost between around $1,500 and $2,300 nowadays. The next high-ticket items are the clutch and heels, both from designer Charlotte Olympia. (Do we detect an homage to the honoree of the day, Princess Charlotte?) The designer's clutches usually run around $600 and her heels will set you back $750 per pair.

When you're the future queen of England's sister marrying a billionaire, chances are you wouldn't wear just any wedding dress. And of course, Pippa Middleton predictably didn't skimp on her big day duds. There was a lot of speculation surrounding the designer she would choose for her wedding in May 2017. She ultimately went with British designer Giles Deacon. According to Bridebook UK, the lace dress–specifically designed for Middleton, naturally–had an estimated price tag of over $47,000. 

However, the high-priced items don't end there. Add to that the Stephen Jones veil, again designed specifically for the occasion, which would roughly set the bride back $2,500. Then there's the $5,000 Robinson Pelham Maidenhair fern tiara that adorned her chestnut locks and her Manolo Blahnik shoes. The ivory satin heels with customized pearls cost approximately $2,500. We'll do the math for you on this wedding ensemble: $57,000, more than most couples spend on their entire wedding.

What makes this moment at the 2017 Para Snowball fundraiser the priciest on our list of Pippa Middleton's most expensive looks? One of the smallest items, in fact. Her engagement ring. James Matthews and Middleton announced their engagement in July 2016 and she certainly had proof that she planned to uphold her lavish lifestyle: an Asscher-cut diamond ring that's reportedly worth around $330,000. (It still doesn't compete with Kate Middleton's engagement ring from Prince William, a sapphire from his late mother, Princess Diana.)

And though it seems like small potatoes compared to her finger candy, her smoky navy Self Portrait dress would cost north of $800 for something similar today.

We don't often see Pippa Middleton re-wear looks, as sister Kate does, leaving us to assume that she continues to buy her upmarket items for each event. We can only imagine what the staggering total cost of Pippa Middleton's entire wardrobe must be.