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MILAN — There is no doubt Jake Gyllenhaal cut a dapper figure at the unveiling in March of Bulgari’s latest high jewelry collection, dubbed Eclettica.

He perfectly embodied the role of global brand ambassador. Donning a Bulgari Bulgari watch, on the lapel of his black tuxedo jacket sparkled an Eclettica brooch in white gold with one antique cushion sapphire, fancy-cut diamonds and pavé-set diamonds. Tapped last month, Gyllenhaal joined fellow brand ambassadors Anne Hathaway, Dua Lipa, Liu Yifei, Lisa Manobal and Priyanka Chopra Jonas at the event, but was the only man among them.

The annual showcase for Bulgari’s high jewelry and accompanying watch, handbag and fragrance collections, the gala was held two months earlier this year and followed previous events in the past in Taormina, Rome and Venice. This year’s black-tie gala had VICs travel from all over the world to Villa Arconati, surrounded by the Parco delle Groane, for a cocktail, a dinner under the stunning frescoed vaults of the 17th-century building, and a fashion show that featured live musicians and dancers, 3D screens and models wearing gowns by Francesco Murano, as well as a few male models who donned the brand’s watches and high jewelry pieces.

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Cesare Attolini wool 150’s suit; Brunello Cucinelli cotton lightweight denim Western shirt; Bulgari Octo Finissimo Automatic watch in 37mm extra-thin titanium case, opaline titanium dial with rhodium-plated hands.

Cesare Attolini wool 150’s suit; Brunello Cucinelli cotton lightweight denim Western shirt; Bulgari Octo Finissimo Automatic watch in 37mm extra-thin titanium case, opaline titanium dial with rhodium-plated hands. Danny Kasirye/WWD

Commenting on the appointment of Gyllenhaal, Laura Burdese, Bulgari’s deputy chief executive officer, touted how the actor’s “artistic sensitivity and his ability to create sincere connections with people reflect the very essence of our maison. He brings depth, humanity and purpose to everything he does.”

While the brand had a previous regional male brand ambassador, Gyllenhaal’s appointment reflects a major strategic move by Bulgari, as well as the growing demand among men for jewelry that previously would have been considered for women only. Indeed, Jean-Charles Babin, Bulgari’s outgoing CEO, pointed to the trend as one of the reasons the brand tapped Gyllenhaal and said it plans to increasingly highlight watches and jewelry that might appeal to men as well as women, stressing the company sees some of its designs as “unisex” rather than specifically for men.

The 45-year-old American actor’s body of work spans more than three decades, and includes a BAFTA Award win and an Academy Award nomination for Best Supporting Actor for his portrayal of Jack Twist in Ang Lee’s 2005 “Brokeback Mountain.” Since then he has earned acclaim for his performances in films ranging from “Jarhead” and “Zodiac” to Tom Ford’s “Nocturnal Animals,” as well as “Wildlife,” “The Day After Tomorrow,” “Spider-Man: Far From Home” and the series “Presumed Innocent,” to name a few. He has also performed on stage, for example in the West End production “This Is Our Youth,” and in “Sea Wall/A Life,” which earned him a nomination for the Tony Award for Best Actor in a Play.

Over the years Gyllenhaal has fronted campaigns aligned with his personal passions, such as sailing, for Prada‘s Luna Rossa fragrances, and manual craftsmanship, serving for Ginori 1735 as brand ambassador of the storied Italian porcelain and home decor products maker owned by Kering.

Brunello Cucinelli Malfilé cotton English rib sweater; Prada virgin wool trousers; Bulgari Octo Finissimo Automatic watch, yellow gold case, dial and bracelet.

Brunello Cucinelli Malfilé cotton English rib sweater; Prada virgin wool trousers; Bulgari Octo Finissimo Automatic watch, yellow gold case, dial and bracelet. Danny Kasirye/WWD

In advance of Watches and Wonders 2026 in Geneva — where Bulgari will show its latest watch designs — Gyllenhaal posed for the WWD cover shoot during his quick few days in Milan, in the garden of the Bulgari Hotel. Charming and relaxed, he chatted easily with the photographer, hair and makeup person and even a few fans who stood nearby and called out “we love you” as he walked by.

Here, the actor discusses how he treasures his first watch and the meaning it holds for him, his relationship with Bulgari, his feelings posing for shoots, and his love for Italy.

WWD: Do you remember your first piece of jewelry and your first watch? How did they make you feel?

Jake Gyllenhaal: My first piece of jewelry was a watch I got for graduation from my parents and my grandfather. They all pitched in to get it for me, and that made it mean even more [special]. It wasn’t just a gift, it felt like a reminder of everything it took to get there.

Every time I look at it, I think about the hard work, the long days, and the people who believed in me the whole way. It reminds me of my work ethic, but also that moment of celebration we all shared. I still cherish it today, and it always brings me back to that time in my life.

WWD: When did you first start to develop an appreciation for jewelry and timepieces? How did that begin?

J.G.: I think as a man, I really started to see watches as a way of expressing yourself. Any type of jewelry in general, something simple, can say a lot. In a lot of ways, it feels like an expression of self-respect, and sometimes a way to show your individuality.

I also think there’s something important about the idea of something that shines. Wearing something like that can be a reminder to carry yourself the same way, to show up with confidence and to put your best self forward.

WWD: What do you look for in these categories?

J.G.: I think jewelry is like art, and it’s incredible to look around the world and see how everyone expresses themselves. Jewelry is art, each piece tells its own story. 

WWD: Do you like to change them often or do you prefer to wear always the same pieces?

J.G.: I like to keep things consistent. Everything I wear is really personal to me, and some pieces I’ve kept and worn for years. They hold meaning, so I don’t feel the need to change them often.

WWD: How did your relationship with Bulgari start and develop?

J.G.: The irony is that the very first piece of jewelry I ever bought for myself was a Bulgari watch. I still have it, and I really cherish it. When the company later approached me and showed me the Octo Finissimo, I loved it! I had such a great meeting with the group of women leading it. They spoke about Bulgari as a family, and as a brand rooted in individuality and artistry.

I was taken by their warmth, their intelligence, and their vision to make meaningful changes. I’ve always admired people who want to keep evolving, and it was clear their leadership felt the same way. That made it an easy decision.  

WWD: You carefully choose the brands you decide to endorse, so why Bulgari in particular?

J.G.: Bulgari is a timeless, extraordinary company that has somehow managed to stay true to itself even as it’s grown. That’s a hard thing to do. At the same time, they’re looking to make interesting changes to keep growing, evolving, and reinvigorating the brand, which I found really inspiring. You can feel the brand retaining what makes it unique but also moving in a new direction. 

I love the idea of constantly evolving, staying open to new inspiration, and not being afraid to take risks.

Brunello Cucinelli Malfilé cotton English rib sweater; Bulgari Octo Finissimo Automatic watch, yellow gold case, dial and bracelet; B.zero1 necklace with chain and small round pendant in 18-karat white gold.

Brunello Cucinelli Malfilé cotton English rib sweater; Bulgari Octo Finissimo Automatic watch, yellow gold case, dial and bracelet; B.zero1 necklace with chain and small round pendant in 18-karat white gold. Danny Kasirye/WWD

WWD: What did Bulgari represent for you before becoming an ambassador and how have your views of the brand changed since then?

J.G.: They really do an incredible job of making you feel like family. They’re a very generous group of people, and they’re admirable from the outside, even more so once they welcome you in. I think what really moves me is that there’s a genuine, beating heart at the center of Bulgari, and I’m honored to be a part of it.

WWD: Generally speaking, do you think men are more open to wearing jewelry today?

J.G.: Yes. Very much so!

WWD:  You have deals with two other main brands in Italy, Prada and Ginori 1735. What is your relationship with Italy and how do you choose your collaborations with brands?

J.G.: Prada and Bulgari, even though they’re very different companies, share something really meaningful. They both have a deep respect for art, artistry, the artists themselves and maintaining the craft. They value people who are pushing boundaries and aren’t afraid to take risks, and that’s something I deeply connect with.

There’s also something essentially Italian about both companies, a profound sense of culture, beauty, and passion that runs through everything they do. It’s truly an honor to work with them. I love Italy so much. Any excuse to come to Italy, to be in its culture, connect with its wonderful people, enjoy the food, and immerse myself in the history and architecture. 

WWD:  You are of course used to being in front of a camera, but how do you feel posing for shoots? Have you gotten used to them?

J.G.: The irony is I’ve never really felt totally comfortable with it. I love performing and expressing myself, but I’m not focused on playing to the camera. My love is being able to connect with the other person in a scene, or with the artists around me.

That’s what I really love about it. It’s not the posing, it’s the collaboration and the connection. To me, art is collaborative, it’s all about the people you’re lucky enough to create and connect with along the way.