Tom Marchitelli traded a finance job for fashion. Now he dresses elite athletes in $5,000 suits.

When Tom Marchitelli agreed to make custom suits for NFL player Chase Daniel in 2014, he had a secret: he had no other clients.

Marchitelli, 44, was working with a tailor to make bespoke suits for himself and sharing Instagram photos of his designs for fun. He wasn't a professional — yet.

Daniel, then a quarterback for the Kansas City Chiefs, didn't know that. He'd come across Marchitelli's account and saw sharply tailored suits in vibrant jewel tones and bold prints. He reached out, saying he wanted to "look like the guy in the photos."

Determined to deliver, Marchitelli learned the basics of tailoring, flew to Kansas City to measure Daniel, and returned weeks later with two nearly perfect suits — a royal blue tuxedo for Daniel's wedding and a textured beige set. He walked away with about $6,000 from his first styling job.

"[Daniel] had no idea it was my first time because I walked in there like he was the 50th athlete I'd measured," Marchitelli told Business Insider. "I was confident in myself that I could deliver."

That mindset has taken him from a stylish hobbyist to a designer with hundreds of clients, including NFL stars Travis Kelce and Rob Gronkowski, as well as athletes in the NHL, WWE, MLB, and more.

"Fashion is 100% a sport," Marchitelli said. "When a guy outdoes everybody [with his clothes], other guys are going to whisper in their ear on the side, 'Hey, where'd you get that?' That's why I've continued to be successful."

From fashion to finance and back

Waltham, Massachusetts, isn't the most fashionable place in the world. Marchitelli, though, made his hometown his runway.

Before starting fourth grade, Marchitelli begged his mom to take him shopping for the perfect back-to-school outfit: black jeans and a vibrant purple shirt that would match his favorite Nike sneakers.

"My parents, sisters, and friends told me I was crazy and wondered why I was so obsessed with what I wore," he said. "I always thought that if everyone has to wear clothes, why not try to wear them better than everyone else?"

Despite his childhood passion, Marchitelli never considered a career in fashion. Instead, he attended Boston College in the early 2000s, where he majored in finance. He aspired for a stable career in accounting. Marchitelli said he "probably cared the least" about his style during his undergraduate years.

From 2004 to 2008, Marchitelli worked in a rotational accounting program at Bear Stearns. Then, he pivoted to a "very cushy, 9-5 job" at the hedge fund Taconic Capital.

"I was paid very well, and the people who worked there were great," he said. "I could go to the gym every day when I would get home, and once my wife and I started a family, I'd be home in time to put my oldest to bed."

But the routine eventually got old. "When I woke up in the morning, I wasn't excited to go sit at that desk," Marchitelli said. "I'm a hedonist, I would say. I live for the pleasures in life."

In Marchitelli's case, those pleasures always included fashion.

He had a New York City tailor at the time who would make him custom suits for formal events. Though the tailor said he was doing the best he could, Marchitelli was convinced his suits could fit better.

"I took all the suits he made me, maybe six or seven of them, and I found a tailor in downtown Manhattan who did everything I asked," Marchitelli said. "He chopped all these suits up for me, and I paid attention. I saw that [tailoring] is a numbers game, and I took to it."

A hobby turned career

Scroll through Marchitelli's account, Gentleman's Playbook, and you'll see some of your favorite athletes wearing his designs before big games.

There's Joe Burrow arriving at SoFi Stadium for Super Bowl LVI in a striped, three-piece suit and wide-brimmed hat, and Tyler Seguin in a green bomber suit ahead of the first Dallas Stars game this NHL season.

Each of their looks is drastically different for a reason. Marchitelli doesn't design in a single style or cover his clothes in massive logos. Instead, he focuses on creating subtle yet striking outfits that match a player's personality.

The images on his page now are a far cry from the headless, close-up shots of Marchitelli in suits that used to fill his feed when he created his account in 2013 (back when Instagram only allowed cropped squares). Still, they were enough to attract thousands of new followers each day, including celebrities and athletes.

"I was traveling to Buffalo to see some Sabres hockey players, and when I landed, I had 3,000 new Instagram followers," Marchitelli recalled. "I didn't know what happened until I saw that The Rock (Dwayne Johnson) started following me and liking my posts."

Gentleman's Playbook was meant to be a creative outlet. Marchitelli would share his designs and write fashion-related blog posts on Tumblr during his downtime at work. He didn't bank on it becoming more than a side hustle until he met a former New Jersey Devils goalie who offered to connect him with the entire hockey team.

"I accumulated half a dozen hockey clients, all who lived in the same town as me," he said. And he didn't stop there. Marchitelli began messaging players across the NHL, whether they were local or not.

One hockey player, Evander Kane, who played for the Buffalo Sabres, assumed Marchitelli's suits were the work of a different Tom: Tom Ford. Marchitelli replied that his suits would fit better and cost less than anything from the designer.

"I remember going to work at the hedge fund that day with my gym bag filled with fabrics that I was going to show Evander," Marchitelli said. "He ended up buying eight suits, almost as if he were going to the convenience store and buying chips and a drink."

Whereas Kane had been paying $8,000 for custom Tom Ford suits at the time, Marchitelli said, Gentleman's Playbook designs were running $3,000 a pop. Even now, to purchase one of Marchitelli's suits — and by extension, his expertise — it costs between $3,000 and $5,000 per outfit.

"I realized I could really do this as a business," he said. "I thought: 'This guy just spent $30,000. How many weeks at the hedge fund will I need to work to make what I'll net from this sale? This is doable.'"

How he gets it done

Marchitelli describes the early days of his styling career as "scrappy." He spent hours scouring social media for stylish athletes who might take a chance on his services. Many ignored his messages.

"I had to endure hearing the word no from hundreds of guys, or hearing nothing," he said. "You either get a yes, a no, or ghosted."

"I'd shoot out 200 to 300 DMs a day, and I was lucky if I heard back from one person," he added.

That's no longer the case. Now, many clients find him through Instagram or their teammates and make the first move.

"Yesterday, the head coach of the Jets texted me randomly," Marchitelli said, referring to Aaron Glenn. "He said: 'Hey, I heard you're the guy to make me a closet full of clothes for casual and game day arrivals next season.'"

It also doesn't hurt when a client becomes a household name. Take Travis Kelce, for example. Marchitelli has styled him on multiple occasions since early in Kelce's career.

While Marchitelli said he's never asked a client to tag him on Instagram — and never will — Kelce always did. So when the Chiefs tight end won back-to-back Super Bowls and publicized his relationship with Taylor Swift, Gentleman's Playbook naturally gained more attention.

And it's a good thing Kelce's had Marchitelli on his team. The clothier recalled a styling session in 2018, when the football player asked to wear a suit with shorts to the ESPY Awards.

"I said, 'Trav, I don't think that's the look. If you want to look good, you're going to sweat a little bit,'" Marchitelli said. "He took my advice and wore my favorite suit I've done for him: an electric royal blue set with black paisley print."

The decision paid off. On the red carpet, numerous other athletes wore shorts with their suits, while Kelce, in his more glamorous look, stood out.

"He was very happy that I made that call," he said. "But now that I think about it, where do I get off telling Travis Kelce no?"

Still, many aspects of Marchitelli's job remain the same. He handles the majority of his business himself, completes much of his work from his home office in New Jersey, and travels constantly.

Unlike some of his peers, Marchitelli doesn't do business over the phone, mail out his clothes, or limit his services to one meeting. Instead, he says he'll "be back in your house again" two or three weeks after a measuring appointment with his designs in hand.

It's how he pays close attention to detail, gives clients closer looks at fabrics, better explains clothing fit, and creates cohesive collections.

"I don't care what the flight costs because I need to be in front of them," he said. "I want my guys to get what they are paying for and understand the value in me. They're not just buying the clothes; they are buying me. This business has always just been me."

Style over stability

When Marchitelli jumped into his styling career, his parents and in-laws had questions. Mostly, they were worried that he'd lose the stability of his finance job for something fleeting.

Marchitelli's wife, on the other hand, never doubted that he'd succeed. She supported the career change from day one.

"I didn't need any more assurance than that when I had her believing in me the way that she did," Marchitelli said.

Luckily, the couple had the right idea. Marchitelli has found happiness and financial gains that didn't come as easily with his former career.

"I remember having meetings for my annual bonuses at the bank and hedge fund, and I left dissatisfied every single year," he said. "I didn't think I was being paid [fairly] for the hard work, time, and effort that I put in."

"Now, I'm paid for everything that I pour into my work — fully merit-based," Marchitelli added. "I push harder and harder each day. My foot doesn't leave the gas pedal."

Of course, he's never done. Marchitelli is determined to style more NBA athletes. Despite basketball being his favorite sport, he's struggled to break into the league.

"I can count my NBA clients on one hand," he said, noting New York Knicks player Jalen Brunson is one of them. "It's kind of been the bane of my existence."

The reality is that NBA players rarely wear suits to games. Marchitelli can accommodate and make more casual looks, but the sport's fashion culture leans on designer logos and exclusive runway pieces.

Despite having "little to no traction," he said, Marchitelli follows up with basketball players via DM every year.

"I'm doing fantastic, but if I dip into the NBA the way I've impacted the MLB, NHL, and NFL? Oh boy. Then it might be time to hire somebody," he said.

He's also hopeful that one day he'll snag his dream client, no matter how long it takes. "Whenever I get texts from numbers that I don't recognize, I always, always say, 'Is this Tom Brady?' It hasn't been yet," he said.

Marchitelli has accomplished something truly unique, though. He's essentially assembled the world's best athletes into his own team of fashion superstars. Whether they want a Super Bowl ring, the Stanley Cup, or a World Series title, they all wear Gentleman's Playbook suits proudly.

"I'll never stop trying to grow the roster," he said.