Fedora Shopping With Sean Stellato, the NFL's Proudest Italian-American Agent

🤌🤌🤌🤌🤌🤌🤌🤌🤌🤌🤌🤌🤌🤌

Last year, the NFL focused its attention on two fan demographics I happen to identify with: Swifies (i.e., women) and Italians. This is why, much to my chagrin and amazement, I can now tell you that Travis Kelce is a “tight end” and that Sean Stellato is an agent. I know you know who the first person is. The second, Sean Stellato, made headlines in December when one of his clients, Tommy DeVito, a 25-year-old undrafted rookie living at home with his parents in New Jersey, was summoned by the Giants when the team’s two other quarterbacks got injured.

STAY WITH ME: Miraculously, DeVito led the team to three consecutive wins, one of which was against the formidable Green Bay Packers. It was a nationally televised Monday Night Football game, and when the Giants scored a touchdown, cameras cut to Stellato, who looked like friggin’ Vito Corleone in a black pinstripe suit, gold chain, and fedora. In a moment of pure Mamma Mia bliss, he pinched his fingers like this 🤌🤌🤌 and kissed DeVito’s dad on the cheek.

It was the most quote-unquote Italian-American thing the NFL has seen in a long time, and the internet ate it up like a bowl of mom’s spaghetti. Steven Van Zandt, who plays Silvio on the Sopranos, tweeted that Stellato was “the Silvio of the Family,” meaning the consigliere, or right-hand. With his help, DeVito, who is obviously Italian, landed a deal with Rao’s Homemade Pasta Sauce. Meanwhile, Stellato’s Internet virality took him straight to the National Italian American Sports Hall of Fame and back to the homeland, where he recently handed a custom Wilson football to none other than il Papa, a.k.a the Pope.

Of course, my first thought when I saw this was: I gotta go shopping with this paisan. I was able to get in touch with Stellato this summer when he was in the Tri-State area visiting the Giants’ training camp. (Originally from Boston, he currently lives in Massachusetts with his wife, Krista, and their four daughters, Gianna, Giulietta, Sophia Belle, and Siena Sicily.) He graciously offered to meet me at his favorite fedora shop, Bellissimo, which I was surprised to learn is not in Little Italy but in Crown Heights, Brooklyn.

Founded by brothers Levi and Yossi Chayo in 2017 to cater to members of the neighborhood’s Orthodox Jewish community, where black fedoras are a staple, the brand’s high-quality yet affordable hats soon attracted the attention of those outside their milieu. One day, in 2019, Jamie Foxx reached out. Now, the store’s wall of fame also boats photos of Snoop Dogg, Michael Bublé, Queen Latifah, Floyd Mayweather, Steve Aoki, Jeremy Piven, and, er, Dave Portnoy, among others. Curiously, Stellato, who wore a black Bellissimo fedora on the night he went viral, has not yet made the display.

“We gotta get that on there,” Stellato says in a thick Boston accent, walking straight up to the wall on the day we visit. “Yeah, that’s a good one,” Yossi agrees. “I gotta print that one.” Stellato offers to sign his portrait and provide the store with its own Sean Stellato bobblehead, which comes out this fall and features a fedora.

Bellissimo co-founder Yossi Chayo and Sean Stellato.

“My late grandfather wore a fedora, and I always loved Sinatra and Stallone, or Rocky Balboa,” Stellato explains. His grandmother, Littizza Lillian Stellato, who immigrated from Calabria to Boston and lived with his family growing up, worked in the men’s department at Filene’s Basement until she was 86 and bought him his first suit. “She used to always say that you have to dress for success and visualize yourself in those moments.” 

A former Arena League football player himself, Stellato, who is now 46, started flexing his style muscles on the field as a receiver for Marist College, where he wore frosted tips under his football helmet. Eventually, he replaced the frosted tips with a fedora, and the accessory has been a staple of his wardrobe ever since.

Stellato is obviously on the left.

So, no, it’s not an act. “Fashion is something I’m passionate about,” he says. He’s wearing head-to-toe Armani EA7 sportswear, Rhone pants, Versace sunglasses big enough to rival a VR headset, and a Bellissimo straw hat. “It’s how I express myself, and it gives me confidence. It’s almost like my Superman cape.” 

Getting dressed is his version of a pre-game ritual. “It’s a way to get me in the zone,” he continues. “If you look good, you perform well. My guys take a lot of pride in how they present themselves when they run through the tunnel onto the field, and I feel the same way when I walk into an NFL stadium.”

A little attention also doesn’t hurt in his line of business. “Does anyone know any other NFL agent?” asks Yossi. “I didn’t know the name of a single one [before Stellato]. It sets him apart from everyone else.”

Stellato often builds an outfit fedora-first, matching every other piece with it “down to the shoes.” He’ll wear a straw one in the summer and for more casual occasions, but a black felt one can also help elevate a simple black t-shirt and jeans. The fedora he wore when he went viral was Bellissimo’s “Toscana” style—brim down, as always—with a custom suit from Mohan’s on Madison Avenue. (Stellato’s bobblehead originally wore a fedora with the brim up, and he asked them to re-design it.)

At this point in our conversation, Stellato’s phone goes off. His ringtone is some version of “That’s Amore” by Dean Martin. While he’s chatting, Yossi tells me that Bellissimo’s hats are made in Canada, where his brother Levi lives, and in Tuscany at a factory just a few blocks away from Prada. (“You can hear the CEO’s helicopter go back and forth for lunch,” he claims.) They’re made the old-school way, out of rabbit felt as opposed to “cheap wool.” Stellato designed his own custom version this summer featuring two different colors.

We’re at Bellissimo that day, though, because Stellato’s dog, Capri, chewed up one of his hats, and he’s in the market for a new one. He tries on a Toscana in midnight blue and goes back and forth about the size of the brim, ultimately going with the larger one. “[The Chayo brothers] have really held my hand and educated me, almost like a coach, which has been great through the entire process of upping my hat game,” he says.

When Stellato looks in the mirror, he’s instantly in agent mode. “Oh yeah, I’m ready to negotiate,” he says. Before we leave, he makes Yossi a pitch: Jamie Foxx has his own custom hat called “The Foxx.” Why not make one called “The Agent?” Yossi nods approvingly. “I like that a lot,” he says. Deal. Bada bing.