Elevating the Humble Hairpin

Jenny Walton, an American artist and influencer, is creating heirlooms — or make that hairlooms.

In late September she plans to introduce the four limited-edition hairpins she designed with Gioielleria Pennisi, the first pieces ever created by the family-owned antique jewelry boutique in the Grand Hotel et de Milan.

Emanuele Ferreccio Pennisi, 46, who works in the boutique and is a grandson of the business’s founder, said that the family had been approached with projects many times over the years, but that Ms. Walton’s proposal “encapsulates elegance.”

“Jenny’s idea to create a hairpin together was fantastic; it’s such a sophisticated accessory,” he said. “Many stores produce charms, items that can be produced in mass and are relatively easy to create, but hairpins are niche. And yet in demand.

“The passage of time has restored their allure,” he added. “Younger customers are increasingly asking us for hair ornaments like tiaras and hairpins, especially for weddings.”

If you live, work or pass through Milan often, you may have pressed your nose to the windows of this store, its décor of gilded cabinets lined in red velvet unchanged since 1971, when Giovanni Pennisi, a diamond dealer and collector, opened the doors. (He died in 1999.)

Pennisi’s roster of clients has included Miuccia Prada, the former Gucci designer Alessandro Michele, Nicole Kidman, Kate Moss, and Rihanna and ASAP Rocky, all drawn by the one-of-a-kind baubles from the 1920s through the 1970s gathered from auctions and discreet family sales.

Gherardo Felloni, Roger Vivier’s creative director and a collector of period jewelry, said on a call from Paris that he traveled the world but that Pennisi carried the best selection of antique gems.

“My relationship with the family goes back over 20 years,” he said. “The stylist Manuela Pavesi, who was also a collector, introduced me, and my relationship with antique jewelry started there, in the Pennisi store.”

Yet, until now, the family had never produced a piece of jewelry.

On one warm afternoon in July, Ms. Walton, 33, was channeling Audrey Hepburn in a full white Prada skirt, demure top and bow-topped heels for a visit to Pennisi. She first met the family in 2014 — a couple of years after she graduated with a Bachelor of Fine Arts in Fashion Design from Parsons — while she was on her first trip to Milan and had decided she wanted to see where Mrs. Prada buys her gems.

In 2017, she went to the boutique to choose her engagement ring, a turn-of-the-century toi et moi style. “Sadly, that didn’t pan out,” she said, “but my friendship with the Pennisi family did.”

She moved to Milan in 2021, and last summer bought the earrings at Pennisi that she was wearing this particular day: a pair of Victorian old-cut diamond pendants in yellow gold. Around the time of that purchase, she had coffee with Mr. Pennisi in the nearby Emporio Armani Caffè, and they hatched the collaboration.

Before the pandemic, while she was still living in New York City, Ms. Walton had designed costume jewelry with 1950s daisy motifs and sold them online. Once she was in Milan, she decided to “reconfigure her life, but still wanted to do something with jewelry.”

According to Ms. Walton, the No. 1 question posed by her Instagram followers — who number 366,000 — is how to recreate her signature French twist coiffure. It wasn’t always so. When she started out, photographed from all angles at runway shows, Ms. Walton noticed her hair’s silhouette was on the sloppy side. Her messy bun didn’t cut it. Nor did an elastic-band ponytail.

In 2016, during a visit to Florence, a kindly pharmacy assistant changed her life with a U-shape hairpin and an impromptu tutorial. Since then, her blond hair has been neatly tucked into a twist.

She suggested some elevated versions of the pin to Mr. Pennisi, and they took as their starting point a pair of Cartier hairpins from the early 1900s in the family’s personal jewelry collection: elongated U shapes in tortoiseshell, topped with diamond-accented lacy platinum scrollwork.

“Such hair accessories were popular in the late 19th century when women had long complicated hairstyles,” said Leo Criaco, a senior jewelry specialist at Christie’s in Milan.

But when short hair became popular in the early 20th century, “many pins didn’t survive; sold to gem dealers or broken up for their stones to create something new,” he said. “Those that have, are often crafted from materials like coral, ivory and tortoiseshell,” which are difficult to export because many countries ban or restrict products related to endangered species.

Hair jewelry is “a very chic idea,” said Pamela Golbin, a former chief curator of fashion and textiles at the Musée des Arts Décoratifs in Paris, who noted that the French maximalist designer Christian Lacroix often used such pieces in the late 1980s through the early 2000s. “We haven’t seen that territory used again for quite a long time,” she said, “and it’s a pity because hair adornments have always been quite stunning.”

Ms. Walton and Mr. Pennisi began working on the hairpins in October 2022, selecting four of her designs and settling on a slender silhouette for the basic form.

Determining the best material proved difficult. They wanted a retro look, so they started with Bakelite, a hard plastic popular for everything from jewelry to home appliances in the 1920s and ’30s, but it didn’t work well; then stone, which proved too heavy. Eventually, they settled on acetate from a Milanese supplier. All four designs will be offered in three colorways: black, amber and an ocher that resembles risotto alla Milanese.

Gioielleria Pennisi’s in-house goldsmiths decorated the acetate pins, adding 18-karat white gold and brilliant-cut diamonds from dealers in Lausanne, Switzerland, in totals ranging from 0.7 to 0.2 of a carat, depending on the design.

One hairpin, called Bassotto (Italian for dachshund), was inspired by Ms. Walton’s fascination with chic Milanese ladies as well as their wire-haired dachshunds, which prompted her in March to buy one of her own, which she named Aurora.

Bassano and Duchessa, a design resembling the gate of an Italian palazzo, will retail for 2,900 euros ($3,195), while Lilium, an openwork design that references Ms. Walton’s favorite flower, and Margherite, a daisy composition that is a nod to her former American designs, will be €2,500. Ms. Walton’s compensation will be an undisclosed portion of each sale.

During Ms. Walton’s visit in July, all three Pennisi men who work in the store were on hand. Emanuel Pennisi was joined by his uncle, Guido Pennisi, 80, the founder’s son and now the business’s president and co-owner, who offered guests a spremuta (freshly squeezed orange juice) and opened a vitrine to show some jewelry to a German customer.

And Guido’s son, Gabriele, 47, brought out Madonna’s 2019 “Madame X” album to show guests the cover image of the pop star wearing a pair of Art Deco platinum and diamond earrings she purchased at the shop.

The men patiently conversed in Italian with Ms. Walton, who is still learning the language. Then she decided to model one of her new hairpins and, as they looked on, she fastened the Duchessa design into her chignon.

“The idea is to wear a pin color suited to how much you wish to highlight the diamonds,” Emanuele Pennisi said. “Black is obvious, whereas the ocher is more subtle.”