Toby Tan: Drawing His Way Through Football, Fashion & Life

Main Photo: Tobyato x Guinness (Photo: Ashok Kumar)

 

 

Toby Tan is one of those rare creatives whose work hits you instantly—bold, expressive, full of personality. But long before “Tobyato” became a staple in Singapore’s creative and street culture scene, he was just another Bukit Batok kid sprinting across neighbourhood courts, squeezing every minute of playtime out of the day. Ask him about those times and he lights up immediately. “Primary school recess? We didn’t eat lah, we just played football.” His childhood was never about organised training or CCA teams. It was about The Cage, void decks, street soccer courts, and running until the sun dipped behind the HDB blocks.

 

Football became the soundtrack of his youth. At home, Premier League nights were sacred—Toby and his brother glued to Manchester United. David Beckham’s free kicks, Ryan Giggs’ gliding runs, Paul Scholes’ unreal passing range… these were the players who coloured his early football imagination. But as he grew older, he found himself drawn to someone very different—Park Ji-sung. “He wasn’t in the limelight, but he worked the hardest,” Toby says. That quiet engine-room mentality stayed with him far longer than any flashy moment ever did.

 

 

Tobyato x Nike Airmax stone creature sculpture (Photo courtesy of Toby)

 

Tobyato x Gshock (Photo courtesy of Toby)

 

 

As he entered the creative world, football resurfaced—not on the pitch, but in culture. Toby vividly remembers the period when the Lion City Sailors shook up the scene under the direction of Kevin, better known as Lion City Boy. There was a fresh swagger in Singapore football. Youth energy, music, fashion—it all came together. What stood out to Toby was how Kevin roped in Tell Your Children, the local art collective, to co-create designs and campaigns. For the first time, local football was crossing into street culture through art, collaborations, shirt drops, activation ideas… it felt alive. “It reached outside the usual football circle,” Toby says, and coming from someone so tuned into culture, that’s high praise.

 

That curiosity naturally extended to Singaporeans pushing boundaries overseas. One name Toby speaks about with genuine admiration is Tokyo Verdy Beleza’s rising star, Danelle Tan. He first noticed her on Instagram, drawn to her maturity and composure despite her age. “She’s beyond her years,” he says. Her boldness, clarity and hunger resonate with him—because whether it’s football or art, the courage to step out is what separates dreamers from doers.

 

And that’s where Toby’s worlds start to blend. Football taught him something that unconsciously shaped his creative philosophy: collaboration. He approaches projects the same way he once approached the game—never as a solo dribble, always as a well-timed pass. “The ball travels faster when you pass it,” he says, and that became his mantra. Campaigns, in his eyes, should feel like team goals—many minds, many touches, one shared finish. This is why his projects often feel warm, human, and communal. They carry fingerprints from everyone involved.

 

 

Tobyato x LaLiga x Cheng San futsal mural (Photo: LaLiga)

 

Tobyato x Guinness (Photo: Ashok Kumar)

 

 

That same spirit powered his Guinness jersey collaboration. Instead of leaning into rivalry—club colours, banter, tribalism—Toby flipped the script. His idea was simple but powerful: create a jersey any football fan could wear, regardless of who they supported. The result was a design filled with personality. Three Guinness pints clinking on the chest to symbolise friendship. A Guinness can stylised into a Kallang Wave. A cheeky toucan balancing a pint while perched on a football. Some joked it looked like a Spurs silhouette. Toby laughed. “Not the intention lah!” What mattered to him was unity, not rivalry.

 

When asked whether he’d trade his markers for a pair of football boots if he had the talent to go pro, Toby doesn’t even hesitate. No chance. Football, to him, is joy without expectation. “When it becomes a job, all the shouting, the laughing, the falling down… they’re no longer fun,” he explains. Drawing as a career already took away some of that innocence. Football remains sacred—an escape that must never turn into obligation.

 

Even the name “Tobyato,” which sounds like it went through layers of branding workshops, actually came from a simple playful moment—a Japanese phonetic twist of “Toby’s Art.” No hidden meaning, no grand story. Just Toby being Toby.

 

 

ChivasSG @ Manchester United (Photos courtesy of Toby)

 

 

But nothing in his journey tops the day he literally drew his way onto the Old Trafford pitch. Through a global Chivas x Manchester United campaign, Toby was selected to represent Singapore. He trained at Carrington, played on the Old Trafford turf, and stood on the pitch looking up at the Stretford End—not as a fan in the stands, but as someone on the grass itself. For a lifelong United supporter, it was surreal. “I think I’m the only one in Singapore who drew my way onto the Old Trafford pitch,” he says, before adding with a grin, “and hopefully I can keep saying that for a long time.”

 

That’s the magic of Toby’s story. He may not have become a footballer, but football shaped him—his vision, his values, his collaborations, his identity. He grew up racing friends across Bukit Batok’s courts, and today he’s racing through the creative world with the same fire and joy. His boots never took him to Old Trafford—but his pen did.

 

And honestly, that might just be the most Tobyato thing ever.