How this Hollywood stylist picks watches for A-List clients (from the Rock’s Rolex to Ryan Reynolds’ Omega)

CREDIT – OR BLAME – Joan Rivers for the phrase “Who are you wearing?”

Working the 1991 Golden Globes red carpet with a microphone and a twinkle of mischief, Rivers lobbed the now-iconic, grammatically questionable question at Hollywood’s finest.

Many a celebrity interviewer has since borrowed it.

(Of course, red carpet fashion wasn’t always about “Valentino couture.” Decades before Rivers’ question existed, Janet Gaynor – the very first Best Actress winner in 1932 – accepted her Oscar in a dress from a children’s shop and a pair of brogues. Five years later, Luise Rainer took home the same prize in her nightie. She lived to 104. Draw your own conclusions.)

These days, the question still gets asked – but the answers aren’t just about gowns and tuxedos.

There’s a new conversation starter: what’s on the wrist.

Watch-spotting has become a red carpet sport, and like any good sport, it has its champions.

Timothée Chalamet’s enduring love of teeny-tiny Cartiers dates back to 2022, when he was spotted wearing a rare double‑time‑zone Cartier Tank at a premiere.

Barry Keoghan, Donald Glover and Dwayne “The Rock” Johnson have all played the game too, under the guidance of Hollywood stylist Ilaria Urbinati – who knows that for men, a watch can be the equivalent of a Tiffany necklace or a Birkin bag, the “easy flex” that pulls a look together.

“Without a nice watch, it feels a little . . . naked,” she says.

Urbinati has built her career on that philosophy – and now she’s bringing it to the public.

This week she teamed up with Watchfinder & Co., the UK-based pre-owned luxury watches platform, to launch Stylist in Residence.

Their debut project, The Style Edit, is a 163-piece capsule of standout timepieces pulled from Watchfinder’s vast inventory and grouped into five style moods: ‘Slim and Chic’, ‘Preppy Sports Watches’, ‘80s Power Era’, ‘Bold Colours’ and ‘Action Hero Watches’.

In it, you’ll find icons like Cartier’s Tank Française and Omega’s Speedmaster “Moonwatch,” alongside more unexpected choices – Vacheron Constantin’s Overseas ref. 4500V/110A-B128, Cartier’s Pasha and Rolex’s Yacht-Master II – reflecting Urbinati’s knack for pairing classic appeal with what’s hot in watch world right now.

When it comes to picking the right watch, she says it varies from client to client.

“I have guys who just wear watches to match their outfit,” she says. “And then I have guys who really do their research and know about special editions, special releases, vintage . . . there’s so much out there. With watches they can really go down that rabbit hole. Men love to nerd out on that stuff.”

As part of the collaboration, Urbinati will offer ongoing advice, trend commentary and hands-on styling insights, helping civilian customers choose a watch the same way her clients might select a red carpet accessory – through a lens of personal style.

Late one night this week, Urbinati spoke with me over video call (her video off) en route from a photo shoot in LA, the hum of traffic in the background – from an Los Angeles photo shoot to a Tufnell Park laptop screen, glamour does not always travel.

Esquire: Hello Ilaria. You’re in LA, right?

Ilaria Urbinati: I am. And I’m in the car, which is why you can’t see me.

Can you tell us what you’ve been doing today, or is it top secret?

I’m not sure I can. I’ve been doing a commercial with two of my clients. Styling both guys. It was very last minute. And then I leave tomorrow to London for 24 hours.

Tell us about the Watchfinder project.

I’ve always been a big watch lover. And through my job, watches have become such a big part of styling men. Back when I started, men weren’t really wearing jewellery. Now, I’ve kind of become “the watch girl”. Watchfinder reached out to me, and here we are.

I’ve seen your list of 163 selections. I don’t know if you’re tallied up the brands, but Cartier leads with 23, Patek follows with 22, IWC with 20 . . . down to Breitling with, sadly, just two. Why do Cartier and Patek top the list?

First of all, I love Patek in general. It’s very collectable. It’s a watch that rises in value and becomes a “collector watch”. It’s something you can hand down. I love that aspect. And I think it’s not as trendy of a brand, which I like. They have many beautiful ones, and they have that vintage look that is very happening right now. Because the watch trend has gone much smaller lately, a lot of my clients are gravitating towards Cartier, particularly Tanks. I didn’t count it up, but now that you’re telling me, that sounds about right. What was the third one?

IWC, with 20.

Well, Watchfinder has a large selection of IWC, so there’s a lot of good options. And I broke the watches down by categories. Even though I’m saying small watches are in and people love Cartier, there are lots of other options. Like, if you’re more of a sporty watch guy, what’s the best version of the sporty watch? What’s the best version of something you feel like Rambo in? What’s got an American Psycho 1980s Wall Street gold watch vibe? I tried to have fun breaking down the styles and categories and then finding the best versions for each. Spreading the love around.

What’s the best watch to go for if you want an “American Psycho 1980s Wall Street gold watch vibe”, then?

A gold and steel Rolex is always going to give you that look. And I feel like we’ve picked quite a few good ones.

That’s quite a different statement between a teeny-tiny Cartier and a gold Rolex. When you’re styling someone, how do you choose?

I love a juxtaposition. I love a really sleek outfit with a bulkier watch. That’s one way to go about it. The other way is to keep everything in proportion – skinny lapel, skinny tie, skinny watch. If I was teaching someone who doesn’t know a lot about style, that would be the easiest trick. Then I think if you know what you’re doing, you can play around a little bit. I do like mixing up a slightly more rugged watch with the sleeker look. If you do it right, it’s fun.

For this project you’re going to be styling “civilians”, not celebrities. Will you approach that differently?

It really depends, because you get “civilians” who are very fashion-forward. I like to think that my “sixth sense” is what my value is as a stylist. Being able to sniff out what someone’s style and vibe is and match the styling to that.

How quickly are you able to sniff someone out?

I feel like I can tell very quickly. So, I think it will be fun to meet people and right away try and get a sense of what they’re into, based on impressions. I don’t think it’s that different than styling an actor, because I get actors who are really classic and conservative, and then I get actors like Donald Glover, who are much more out there with their style

You’ve said before that you like to take people “a little bit outside their comfort zone”.

Yes, but it has to be with a boundary where they’re learning and evolving but still feel like themselves and are comfortable in their own skin. That always comes first. When people try something on, they’re often surprised. My motto is “You don’t have to wear it, but you have to try it.” Try it on! A lot of times, guys will be like, “Wait a minute. You’re right, this does look good!”

How do you go outside the comfort zone with watches?

You do get guys who have always worn one brand and are stuck on that. You like Cartier? Well, what about Vacheron? What about JLC? I feel like guys always know the same three brands. So, it’s fun to teach them… not that I know everything there is to know about watches. Then there are some clients – James Marsden, for example – who are giant watch nerds, and they teach me so much. The watch world is super-nerdy, there’s no end to it.

This thing about men’s watches on the red carpet is fairly new. No one used to care. When did it start?

I feel it was around five years ago. During Covid, a lot of people really started to collect watches. Rolex, for example, couldn’t keep any watches in stock. People were at home and going down rabbit holes and researching and getting excited about it. A lot of art was sold during Covid. My mother is an art dealer, and I always say that collecting watches is not that different from being an art collector. In fact, I have to find special watches for art dealer clients sometimes. They’re both people who really understand what they’re purchasing.

How do people’s choices differ when they’re borrowing a watch?

People get to play around and try a lot of different styles, because it’s less of a commitment, right? You’re borrowing a watch for a night, might as well go with the craziest watch you wouldn’t normally wear. But, then, when you’re purchasing a watch, that’s a different story. And that’s where I help them and try to educate them a little bit more on what makes a watch a good purchase and a good investment. But equally you get guys that don’t care about that. They just want the coolest watch for the moment.

The two red carpet names who really kickstarted this trend seem to be Timothée Chalamet and Barry Keoghan. Would you agree?

Yes. And also The Rock. I feel like every time he wears a watch, it gets written up.

Why do you think that is?

There’s a certain type of demographic of guys that are looking at what he’s wearing. It’s the guys at the gym, the big, bulky guys, who are, like, “Oh, well, I’m a big, muscular guy who didn’t think I could wear fashion, but look at Dwayne doing it”. When I first started out with Dwayne, he’d always be wearing these giant watches. And I think we’ve kind of played around with the idea that it doesn’t always have to be that. And I think guys look at that. I think that has influence.

Anyone else?

Ben Affleck had that little watch J.Lo gave him that everyone lost their mind over. I think when you have guys losing their mind over a watch in the press, that tells you a lot about how much it’s changed. Who else has a lot of influence? Timothée Chalamet and Jacob Elordi probably have a lot of influence on young guys getting into watches. And then also Rami Malek. He’s a big Cartier guy. Then I think Austin Butler, who also wears Tanks a lot [he’s now a Breitling ambassador]. There’s a lot of different guys influencing different demographics, and they’re all wearing a lot of, like, crazy watches.

You dress Barry Keoghan, right?

Yeah, he’s a big watch guy. Granted, he’s got a deal with Omega, so he wears Omega. But he’s always rocking really wild Omegas. The wilder the better. I think people look at that. Especially when he was doing his big awards runs. All of that adds up.

Does Barry choose the watch, or do you?

I narrow down, and then he picks from there. But I know what he likes.

What’s the watch you’re proudest to have put The Rock in?

He used to wear a lot of Panerai, but now he has a “root beer” Rolex – it’s so sick. He found it himself, and I was so impressed – the student becomes the master! You always see the “Sprite” ones, the “Pepsi”, the “Coca-Cola” [Rolex nicknames come from their colours – green/black “Sprite”, blue/red “Pepsi”, red/black “Coke”] – but now he’s got this beautiful brown-dial “root beer”. I just saw it a few days ago, and I think it’s pretty fun that he got there himself, you know?

No teeny-tiny Cartier for The Rock?

We’re not quite there yet. Although he’s got two big events coming up and – I think I can say this – he’s going to be wearing Cartier for the first time.

Big news.

You heard it here first. It’s a Santos. For anyone who likes a Tank, but is a little too big for it, the Santos is a really nice option.

Increasingly, celebrities have deals with watch companies. Does that make your life easier, or harder?

The ones who don’t have skin in the game just get to wear what they like. Guys with contracts have to show the watch – which, as a stylist, can sometimes be challenging because they’re wearing a suit a lot of the time. And I can’t control whether the watch gets seen or not. [For example, being visibly promoted on the red carpet is often a stipulation of the ambassadorial role.]

This is where seasoned pros adopt one of a small repertoire of classic wrist poses – hands held together at the waist, revealing two-inches of cuff; or the watch arm awkwardly positioned across the chest, as if expecting a bird of prey. Will Ferrell recently sent up the whole I-am-wearing-an-important-watch thing up for the silliness it can be.

That was hilarious.

Obviously the point of watch ambassadors is that they sell watches. Have you noticed a spike in sales after specific watch placements?

I don’t know. I can tell which clients move merchandise more than others. Like, I would say Ryan Reynolds – everything he wears, everyone goes out and buys it. There’s something about Ryan that is very relatable to guys. It’s very doable. It’s realistic, approachable. I always hear back from brands, “Oh, we sold out of that jacket ten times after he wore it.” And in DMs, I get more requests from people about what Dwayne is wearing than almost anyone else. And I think the reason is, again, there’s a whole demographic of men out there that fashion has ignored. People think of fashion and they think of, like, a skinny little rail guy. I think Dwayne has an influence in a certain type of guy that maybe feels like he’s been left behind by fashion. And we’ve reframed that for them, hopefully.

How have you done that?

Without being boring or too classic, it’s very approachable, right? You’re like, “He’s wearing a green suede trucker jacket. I could wear that.” You know what I mean? Like, it’s very doable.

It’s not the Met Gala.

Exactly. On the other hand, I dress Donald, and he’s the guy where I hear people say “Well, I want to be fashionable but I can’t pull off what he’s pulled off!”

What’s the most stress you’ve gone to, to get a watch?

Oh boy, it’s like, every day, you know? It’s always like, “This client’s going to Barcelona for a premiere tomorrow. Can we get them the watch?” So, we’re always on the phone trying to get these last-minute watches found. And it has to be the right watch, and it has to get there on time for the premiere. It has to get to a certain city. I can’t think of a specific watch because that’s my life every day.

What’s the most stress you’ve gone to, to get a watch?

There are very complicated rules about what watches can leave which country to go into which country. For example, when Aaron Taylor-Johnson was doing those two huge press tours back-to-back for the Marvel movie [2024’s Kraven the Hunter], and then he went right into Nosferatu, and he had, like, a premiere in a different city every day. He’s got an Omega deal. And Omega is really strict about the watches travelling. We were having to deliver a different watch to each country every day. Sometimes people don’t understand the logistical aspects of being a stylist!

A celebrity probably wouldn’t turn up to two premieres wearing the same clothes, but what about watches?

It really depends. Sometimes we’ll go, “Here’s your watch for all your press days and here’s your watch for all your premieres.” Or we’ll say, “Here’s your watch for all the London dates, and then here’s your watch for all the New York dates.” There are different ways to go about it. We try and switch it up as much as possible. Also, some guys are freaked out about travelling with a ton of expensive watches. I had a guy give me an IWC watch back once because he found out how much it was. “That’s terrifying! I don’t want to travel with that!”

Talk me through a typical selection process.

We just had [Freakier Friday/ Top Gun Maverick star] Manny Jacinto, right? He really loves a Vacheron. And I found a really beautiful one that he liked. So, they sent it to me, and he was allowed to travel with it, and he wore it for a bunch of the press. But then, I said, “Here’s your black JLC watch to wear with all your black and grey, cool-coloured outfits. And here’s your white gold Vacheron that you can wear with all your navy and blues.” We’ll usually pick a black, a brown, a gold and a silver. But sometimes we are really specific about which watch, with which outfit. And then sometimes, if you get a guy like Manny who knows a lot about style, and knows a lot about watches, then you’re just, like, “Here are three watches – pair them to whichever outfit you want.” So, it really just depends.

Does anyone try to keep them?

That’s a constant thing. Asking “Can they gift this?” Barry definitely tries to buy or keep every Omega watch.

Surely Omega can help Barry out? He’s their ambassador.

Every press tour with every single client… they’re either trying to keep the watch or buy the watch. I’m sure Manny will try and bag that Vacheron from Watchfinder. It’s pretty common. Like, weekly.

That means you’ve done your job well. Is this red carpet watch mania going to continue, do you think?

I think the watch-mad thing will grow and grow and grow and grow and grow. Because at this point, I don’t think that’s a genie you could put back in the bottle. But I think trends, and what’s cool – like the “mini” watches– will pass as a dalliance.

Okay.

The bigger wrist space watches will come back. I think it’s going to change. It’s like pants [i.e. trousers]. Skinny pants were repeated to death, and now all the pants are wide. But I already see guys starting to get sick of that trend, and they’re starting to go back to skinny pants. And I think watches are no different, you know?

We should prepare for the return of the wrist frisbee?

It’s going to happen. I mean, that’s how fashion works, right? It swings back and forth. That’s how the industry survives. “I’ve got to go rebuy a whole closet full of pants.” Otherwise, it would be, like, “I bought my skinny pants, and I’m good for life.”

And where’s the fun in that?

Exactly.

---

This story originally appeared on Esquire UK.

Related:

The story behind Pierce Brosnan’s vintage 1945 Girard-Perregaux watch

MoonSwatch to Seamaster: inside Daniel Craig’s Omega watch collection