Jenny Walton Ignites a Trend for Diamond Hairpins

The delightful illustrator collaborated with the legendary vintage
boutique Gioielleria Pennisi on a capsule collection

By |

There are some fine jewelry styles that seemed like their glory days were done forever. They were so linked to certain fashion moments when those periods passed, the silhouettes fell out of favor too. Bold gem-set brooches, for example, dominated the first half of the 20th century then pretty much disappeared as women dispensed with the formal ladies-who-lunch-fashion looks the jewels matched. Flash forward to a few years ago when men started sporting the same brooches from back in those days on their suit jackets and bing, bang, boom, the style is back in a big way. 

Diamond U shape hairpins are another jewelry silhouette that has been long gone. I am not referencing diamond clips or barrettes, headbands, or bandeaus. I am speaking specifically of U shape hairpins with long arms leading up to a curved section on top set with diamonds. From around the 1890s to the 1910s, women used the hairpins to light up and secure elaborate updos. During the Edwardian era supreme jewelers like Cartier made extraordinary diamond hairpins. The style was rendered useless in the 1920s when women chopped their long locks into short bobs. 

A selection of the diamond, white gold and acetate hairpins Jenny Walton designed for Gioielleria Pennisi in Milan. (Courtesy Instagram @jennymwalton)

Well, now the diamond U shape hairpin is making a comeback thanks to the delightful illustrator and influencer Jenny Walton. Over the years, Jenny has designed a few accessories including a fun hat and costume earrings with a joyful daisy motif for the legions who stan her elegance seen perpetually in street style coverage from the fashion shows she attends in New York, Milan and Paris, as well as on her Instagram. For the hairpins, Jenny teamed up with Gioielleria Pennisi, a family-owned vintage jewelry boutique in Milan where she relocated a couple of years ago. 

Established in 1971, Gioielleria Pennisi is situated in the Grand Hotel de Milan and has long been a destination for luminaries who love jewelry. Miuccia Prada, Kate Moss, Rihanna and A$AP Rocky have all shopped or worn treasures from the establishment. The collection of jewels that attracts the tastemakers, range in date from the 18th century to around 1950. Remarkably, the collaboration with Jenny Walton was the family’s first foray into creating jewelry. 

Jenny Walton wearing one of her diamond hairpins and posing in front of the display of her capsule collection at Gioielleria Pennisi in Milan. (Courtesy Instagram @jennymwalton)
Jenny Walton wearing one of her diamond hairpins and posing in front of the display of her capsule collection at Gioielleria Pennisi in Milan. (Courtesy Instagram @jennymwalton)

The concept for the diamond hairpins truly started for Jenny around nine years ago. “I was in Florence on one of my first trips to Europe and I went into an old Farmacia [pharmacy] and saw hairpins and accessories unlike any I had ever seen in America,” explains Jenny. “The woman working there showed me how to put my hair up with one and I have been using one ever since.” 

Jenny’s chic French twist is part of her signature ladylike style filled with A-line skirts, kitten heels, pullovers, clutches, and statement jewels. “When I moved from New York to Milan a few years ago, I wanted to start making jewelry again, but I wanted to do something very small, special, and specific to me,” explains Jenny. 

Once she decided it was going to be hairpins, Jenny went to Pennisi, a store she has frequented and shopped at for almost 10 years, to see if they would be interested in the idea. They loved it and pulled a Cartier U shape hairpin with diamond and platinum details out of their archive collection as a first point of reference. “We have long admired Jenny Walton’s unique style and were thrilled at the opportunity to bring her vision to life through our craft,” says Emanuele Ferreccio Pennisi, Partner of Gioielleria Pennisi.

Once they agreed to the concept, Jenny came up with a few different diamond and white gold motifs to decorate the amber, black, and ochre acetate hairpins which were made by artisans in Milan who work on custom designs and repairs of vintage jewels for Pennisi. 

Rendering of the diamond dachshund hairpin designed by Jenny Walton for Gioielleria Pennisi in Milan

A diamond dachshund wraps around the top of one of Jenny’s hairpins. It is a tribute to her love of the small dog breed and her dachshund, Aurora. 

A diamond Lilium flower on another hairpin style is a celebration of Jenny’s favorite flower. And a three daisies hairpin is a tribute to her first jewelry collection. 

The Duchessa hairpin diamond design echoes the ironwork on a gate of an Italian palazzo which is a hat tip to the architectural wonders of Jenny’s adopted home. 

Display of diamond hairpins and illustrations by Jenny Walton at Gioielleria Pennisi in Milan. (Courtesy Instagram @jennymwalton)

The capsule collection of diamond hairpins is available at the Pennisi boutique and online. They range in price from approximately $2,600 to $3,000. Clearly the jewels are an investment but they are also a major upgrade from claw clips or scrunchies. 

In consideration of all the interest in Jenny Walton’s refreshing sense of polish, I like to think a return of the diamond hairpin on a broader scale is absolutely possible. Just consider what happened to the brooch.