Becoming A Boss: The story of Matteo Berrettini is one of connection—to his upbringing, to his fans and, most importantly, to himself

When he was 16, Matteo Berrettini’s wardrobe rarely strayed from the cliché closet of a high school adolescent: t-shirts, jeans, shorts and sneakers. He might dress it up marginally on nights out with friends and on special occasions, but high fashion wasn’t on his radar of interests. In the classroom, Berrettini was a walking advertisement for skinny jeans, and when he tried to change up his appearance, it usually backfired.

“Once I tried to wear these trousers that my mom got me,” he says. “They were more baggy. I remember getting in the class at high school, and a couple of my schoolmates made fun of me. I never wore those trousers again.”

A decade later, Berrettini has long ditched improperly-sized slacks and tight denims for a sophisticated, smooth style. So mature is the transformation that the strapping 26-year-old has become an ambassador for one of the world’s leading fashion houses: Hugo BOSS.

The idea of partnering with a brand of this caliber hadn’t crossed Berrettini’s mind, though his nonna Lucia never doubted it for a second.

“My grandma, of course, she spoils me. She still thinks that I’m the most handsome guy on the planet. I guess all the grandmas think this about their own,” he laughs. “But I never imagined something like that. I never pictured myself being on billboards all over the world, in such a big campaign for them.

“My family sends me pictures with my face everywhere. So it’s really nice.”

It’s a cutting-edge collaboration, with Berrettini the first tennis player to wear BOSS in competition. He signed on with the German company before the start of the 2022 season, after becoming the first Italian man to reach a Wimbledon final. He’s reached No. 6 in the world rankings, won five titles and made deep runs at all four Grand Slam tournaments.

But beyond the looks and results departments, it’s Berrettini’s inherent qualities—rooted from his childhood—that drew executives in.

“His spirit and attitude, which make him more than just one of the best tennis players in the world, are incredibly impressive,” says Daniel Grieder, CEO of Hugo BOSS AG. “Matteo incorporates what a boss stands for today: showing a strong will, making the right decisions and inspiring people all around the world.”

The elder of two boys (his brother Jacopo is two-and-a-half years younger) to tennis-playing parents, mom Claudia and dad Luca, Berrettini is a courteous, engaging and family-oriented fella. He walks the line of being confident and charming without crossing over to cocky and condescending. It’s an attribute the Rome native assigns to how he was raised—to simply be himself.

“At the end of the day, I’m just a guy hitting tennis balls and doing it pretty well. That’s all I’m doing,” he says.

“I don’t feel like I should be treated differently or that I am someone special in other terms. You have to be kind. You have to have good manners. And that’s what I’m trying to do.

“I created my player side to be confident. When I step on the court, I believe in all the work that I put in. All the years that I’ve practiced and trained, they’re paying off. So that’s where I take my confidence from. It’s important to feel that you can beat your opponent, because nobody’s giving you anything for free.”

To Berrettini, his growth from boy to boss was a state of mind that required years of patience and faith. During his junior days, distinguished performances that screamed future leader were in short supply. He wasn’t a highly-touted prospect making waves in major tournaments. As fellow ATP pro and countryman Lorenzo Sonego recalls, there was nothing to suggest his future best friend on tour would morph into an imposing, physical force.

“When we [were] young, we expected nothing. We were really bad in the tennis,” he says. “When we played the Provence Cup (in Italy), we were 12. There, our relationship was born. I was really small. Matteo as well. Now, he’s almost two meters.

“He’s still a funny guy, but the mentality has changed for him. He wants to win every match.”

Berrettini pressed on, even after losing his first six main-draw attempts at the Futures level—the bottom tier of pro tennis. Admittedly tired the summer after finishing up high school, Berrettini maintained trust in coach Vincenzo Santopadre, as the two continued sketching out his identity on the baseline. Rather than risk pushing his student into burnout by overplaying, Santopadre focused on the long game, investing in development. The centerpieces of Matteo the player were two dynamic features derived from his favorable height: his serve and forehand.

“When we started working together, [for Santopadre] it was really important to create a style that I had on court. It was really important to focus on my weapons,” says Berrettini. “After that, you shape the whole player around it.

“I had to be explosive. I had to be strong. I’m not really the guy that is running a lot, so I need to try and make them run.”

Three seasons after turning pro at 19—late by today’s standards—Berrettini saw their plan come to life. In 2018 he secured his first tour-level match win, in Doha; six months later, he clutched his first ATP trophy on clay in Gstaad. A major splash came the following year: Berrettini advanced to the US Open semifinals, after adding two more titles to his collection. At 23, he qualified for the 2019 ATP Finals.

At the end of the day, I’m just a guy hitting tennis balls and doing it pretty well. That’s all I’m doing.—Matteo Berrettini

While a hernia-groin injury hampered this rapid rise before and after the COVID-19 shutdown in 2020, Berrettini and his team used that time as an opportunity to better understand how much tennis is too much. When we spoke at the start of the 2021 season, Berrettini said in Antalya, Turkey, “The amount and the level of matches that I played during 2019, maybe my body wasn’t ready to figure it out.

“I’m pretty heavy, I’m big. So I have to figure out how many matches, how many practices I have to do.”

At 6’5” and a shade over 200 pounds, Berrettini owns one of the more substantial frames in today’s game. When he’s not wearing a backwards cap, slick dark-brown curls complement expressive eyes that command attention. Slender calves and ankles are a contradiction to the robust upper half of his figure, a genetic shortcoming he’s even poked fun at. His idea of artistic expression isn’t carving a flowing forehand or booming backhand—it’s the five marks inked on his body.

“Tattoos are art in the most beautiful way. I really love all my tattoos,” he says proudly. “I have one guy that did all of them. I’m really close to him; I trust him and we work with ideas together. That is art.

“They all have meaning, mostly my family. I have the date of birth of my brother for one. So many symbols that mean something for people close to me. I can tell you that the fifth one is not going to be the last one.”

If there was a point where Berrettini tattooed his name on the tennis scene, it was the summer of 2021. Having been sidelined with an abdominal injury for two months, Berrettini compiled a promising stretch on clay that included a title in Belgrade, his first Masters 1000 final in Madrid, and a maiden quarterfinal at Roland Garros. And when it came time to switch surfaces, the grass was even greener.

Berrettini broke British hearts when he eliminated three home favorites en route to the London Queen’s Club title, then carried that momentum over to a historic effort at Wimbledon. Six matches later, he emerged as his nation’s first men’s Grand Slam singles finalist in 45 years.

An unstoppable Novak Djokovic ultimately denied his bid for further accolades, though Berrettini believes the knowledge gained from the opportunity is as invaluable as it gets.

“There are small adjustments I can improve in order to be a better player. But one of the most important things is the experience, playing the most important tournaments for many years and playing the most important matches,” he says. “For semis and finals, you need the experience in order to win these kind of matches.

“I think my game is stepping up every tournament. Every week, I feel I’m playing better. Of course, I have my weapons and I have my weaknesses, but it’s all about experience and having the chance to play against the best guys in the world. That’s going to make me better.”

When he took the microphone to deliver his runner-up speech at Wimbledon, Berrettini gave congratulatory remarks to Djokovic and reflected on his stellar grass-court campaign. Then the comical side that Sonego referenced came out to a universal seal of approval.

“I couldn’t ask for more. I mean, maybe a little bit more,” he gestured with a big grin to a cackling crowd.

Berrettini later said, “For me, this is not an end. It’s the beginning, hopefully, of a great career,” as applause soon roared.

One person who connected with Berrettini in that moment was Trey Laird, an advertising authority whose company has worked with BOSS on marketing campaigns. As Berrettini shared with GQ Australia in February, “I remember talking to Trey. And he said, ‘I saw your speech when you lost at [Wimbledon] and I said I really would like to have this guy with me.’”

By January, the first tennis collection, BOSS X Matteo Berrettini, was unveiled. Photo shoots are a customary commitment for sponsors and publications, but as Berrettini soon discovered, none were at the level of this new cooperation. Early call times and 12-hour days are expected, and destinations like New York, Dubai and Los Angeles are the norm when it comes to the asks of working with a major brand as a global ambassador.

Comfortable from their first day together, Berrettini is no stranger to the camera. And while he feels “genuine” in front of the lens, his eyes have been opened to the details that go into the degree of execution with this visual art.

“I learned so much from this world—that a lot of people are behind the scenes. You just see the picture most of the times,” he says. “But when you’re doing shoots, there are 40, 50 people working for just one shot. So it’s really cool. It’s something that you have to get used to.”

In his first major event wearing the line, Berrettini flexed his muscles during a pair of five-setters against Carlos Alcaraz and Gael Monfils to reach his first Australian Open semifinal. The reaction to his tennis line has been positive across the board, and with over 1.3 million Instagram followers, Berrettini is eager to reach an audience away from the court.

“That is the ultimate goal that I have, to inspire others,” he says. “Especially the kids and younger generations. It’s very important.”

Of his first five trips to the quarterfinals and beyond on the major stage—including four in a row, heading into Wimbledon (he missed Roland Garros and the rest of the European clay-court season due to a right-hand injury)—only Djokovic and Rafael Nadal have beaten Berrettini. The tagline of BOSS’ spring/summer 2022 global campaign, where Berrettini debuts as part of a “new era,” is one that resonates with the now established ATP standout: “Be Your Own BOSS”, it encourages. “Every one of us is the author of our own stories.”

How Berrettini tells his story ultimately lies within. But should Matteo stick with what’s worked for the first 26 years of his life—being himself—he may soon grace billboards as a major champion. Nonna Lucia already sees it.