Caleb Simpson—the guy on your FYP asking people how much they pay for rent—has been inside hundreds of apartments. The content creator describes his work as “this generation's MTV Cribs mixed with Anthony Bourdain.” He’s been into filmmaking for 10 years, but it wasn’t until 2022 that he found his niche. Today, millions of viewers flock to his videos not merely for a glimpse into others’ homes, but for the authentic stories his subjects share.
In GAP’s “The Gift You Give,” Simpson swaps the one-bedroom studios for the streets of NYC to embark on a different mission this holiday season: spotlighting local heroes who give back to their communities. Connecting with three creatives, he uncovers how they use their gifts to pour back into those who have supported their unique journeys.
For St. James Joy, a father-son DJ duo composed of Jo Vill and his son Chad, it all started during one of the city’s loneliest periods: the COVID-19 pandemic lockdowns. Amidst the fear and uncertainty, Jo’s wife Gail Bryan-Vill would lead a 7 p.m. cheer for essential workers every night. One day, she invited her husband and son to queue up a few of their songs on a Bluetooth speaker, hoping their musical prowess would make the neighborhood feel more connected.
“Those few songs turned into a 15-minute set, then an hour set, and eventually a full-fledged daily block party,” Chad explains. While the St. James Joy block parties continue today, they’ve also brought their music mixes to food drives and park gatherings, sparking camaraderie at sites of service and community-building.
As they offer Simpson a sample of the DJing experience, the trio is clad in GAP apparel—Simpson in a VintageSoft logo hoodie layered under a coat, Chad rocking a leather jacket, and Jo staying warm as he spins in a wool-blend bomber jacket. “Just like GAP brings people together through timeless style, we bring people together through timeless sound,” the younger Vill notes. “We both share the same mission: making people feel seen, confident, and part of something bigger.”
Giving others space to feel seen is also the mission of poet Shana Roark. Looking especially literary in GAP’s denim chore jacket, she’s sitting at a table with a typewriter and a stack of crisp paper when Simpson strolls by. They instantly connect, which shouldn’t feel too surprising given that they both talk to strangers for a living—although she, predictably, describes her job more artfully. “I’d say my gift is translating emotion into language: Taking what someone feels but can’t quite say and turning it into words that feel true.”
She and Simpson take a pause in the park as she writes an impromptu piece for him. For the last six years, the writer has generously offered personalized poems to anyone who takes a moment to sit and share their story with her. “Like GAP, I try to bridge worlds: art and everyday life, vulnerability and strength, strangers and connection. We both believe in showing up for people, in simple, genuine ways that make the world just a little warmer.” Through the act of giving, Roark has also become a recipient of authentic conversation, connection, and community.
“When you write for strangers, you learn that everyone carries something tender they rarely get to say out loud,” she says. “It’s changed the way I move through my neighborhood — I listen more, I notice more, and I feel a deeper sense of belonging.”
There’s one more stop on Simpson’s tour of New York’s homegrown heroes: a vibrant tiger mural for the annual art fest BedStuy Walls, done by Kamille “OG Millie” Ejerta. Art has always been tied to community for the introverted muralist and creative director, helping her come out of her shell. A former college basketball player, she admits she spent most of her time off the court customizing friends’ shoes and jackets. “What encouraged me to begin sharing my talent was actually positive reinforcement from friends and family,” she adds.
Careful not to get paint on her GAP CashSoft beanie, she crouches to add a finishing touch to her latest masterpiece while Simpson watches on. The finished mural is an act of cultural reclamation, a conversation piece bringing neighbors together to talk, and a memento that can be shared with generations to come. “My hope is to inspire the youth to feel empowered that they can do this too,” Ejerta shares.
Sharing a creative work or a moment is how we’re reminded about what we all have in common—and that’s where community starts. The Vills do this with their music, Roark with her poems, Ejerta with her murals, and Simpson, too, with his intimate house tours. GAP takes clothing as its medium, connecting generations with classic, comfortable styles that empower free expression.
Simpson sums it up nicely as he reflects on what he’s learned from these local heroes who show up and share their gifts every day. “If you're willing to put yourself out there, create something, be vulnerable, you have no idea the profound effect it could have on the community—how it could just add a smile to their face,” he says. “And sometimes that's all people need, you know?”
Click here to unwrap more from GAP this holiday season.
