Anatomy of an Investment Piece: Penelope Chilvers Long Tassel Riding Boots

The “Kate Middleton effect” is very real. Much like Diana before her, the current Princess of Wales can make or break a fashion brand with a single royal style moment. Whether it’s a smart blazer or a chic pair of heels, Middleton’s fashion choices are so well-considered (and thoroughly scrutinized by the press and public alike) that any well-placed garment is guaranteed to sell out — and have a long life in “best of” roundups and Instagram fashion mood boards for years to come.

Perhaps no one understands this power of royal dressing better than Penelope Chilvers. The British accessories designer, whose titular brand is best known for timeless leather designs and functional footwear, has been outfitting Kate Middleton since the very beginning. 

“The first time she was photographed wearing our boots was the day Prince William proposed to her,” explains Chilvers. The boots in question, the brand’s Long Tassel Boots, would become something of a signature product for Chilvers and a hallmark of Middleton’s sporty-classic style. 

“The photo of her with Blenheim Palace in the background went viral,” Chilvers explains. “Our new princess was introduced to the world in her Long Tassel boots.” The rest is, as they say, fashion history: “I will never forget that day. The phone did not stop ringing, and of course, we sold out in minutes.” 

Chilvers still sells those very same boots, and since their first public appearance almost two decades ago, Middleton has been photographed in the shoes more than a dozen times, re-wearing them time and time again throughout her career as a working royal. 

Today, the iconic boots are back in the spotlight thanks to an upcoming appearance in The Crown, but to be honest, they never really left. After all, there are few pieces more classic than an English riding boot (especially one with the Middleton stamp of approval).

Read on for all the details about Penelope Chilvers Long Tassel Boots.

The History

Chilvers’s brand was born from her lifelong “love affair with Spain,” which, in fashion terms, means a passion for Spanish leather. “In my twenties, while living in the hills above the city of Barcelona, Spain, I used to ride [during] my lunch break,” remembers Chilvers. “I commissioned a bootmaker to make me a pair of riding boots to my own measurements and design features.” 

Those features – including a tread sole for all terrains, buttery Spanish leather, and a flattering close-to-the-ankle cut — became the inspiration for her line and its most beloved style. Released 21 years ago, the Long Tassel Boot remains the most iconic version of the English riding boot available in fashion today, built as much for cool ‘fits as all-weather functionality. The brand’s website puts it best: “often imitated, never surpassed.”

The Craftsmanship

Today, the handmade shoe is still produced with the unmistakable craftsmanship of Spanish artisans. According to Chilvers, it takes over 70 touchpoints and two days to create each pair. “The hides are all picked from Gold Rated local tanneries in Spain,” explains Chilvers, giving each pair a unique imprint. “They all have slight color variations due to their natural qualities.”

It’s this close attention to detail that makes a pair well worth the $695 price tag. From the gorgeous scalloped zipper detailing to Penelope’s signature “conker” shade of leather, the Long Tassel Boots are designed to stand the test of time. Plus, features like their Goodyear Welted Commando rubber soles and the fact that they’re soled using 200-year-old machines means they’re built to last, too.

The Appeal

Just take it from Kate: the draw of Penelope Chilvers boots lies in their versatility. “From climbing a mountain in Bhutan to cleaning up the beaches of Wales to promoting the conservation of national parks and wildlife in Canada to visiting children’s schools, they are her go-to boots for casual, country styling,” the designer explains. 

Back when she first released the design in the early 2000s, Chilvers says women wore their riding boots with tucked-in drainpipe denim or floaty dresses. But, the accessories designer stresses that this effortless approach to styling is exactly what makes her riding boots so popular. “So many of our customers say they don’t need a new pair because they love their old pair,” explains Chilvers, citing Cate Blanchett as one of the boots’ many famous fans. “They become dependable old friends.”

What’s next for the world’s most famous pair of riding boots? They recently got an ultra-waterproof upgrade (“The perfect boots for snow and icy conditions with the grip sole,” says Chilvers) and an upcoming feature in the second half of the newest season of Netflix's The Crown, which (you guessed it!) focuses on Kate Middleton and Prince Willaim’s budding romance. “I’m delighted that these beautiful boots, which launched my own career, are playing an important role on TV,” says Chilvers. “They have stood the test of time as a strong design and deserve recognition.”