Men’s fashion and the military have a lot in common, if you ask Derek Questell. After serving in the Marines for 10 years and four deployments, Questell now tailors custom clothing from his Charlottesville home, calling the enterprise Tailored Quest.
“It’s in my blood, my Italian heritage,” says Questell. “My dad gave me my first suit when I was 15. He said, ‘Son, always have a well-tailored suit. It’ll never fail you.’” Questell, who grew up on the coast of North Carolina, tells stories of watching his father build guitars for 45 years and cooking alongside his mother, whom he worried about upsetting when he enlisted two years after the Iraq invasion—a “no-brainer,” he says.
After joining the service, he worked his way up the ranks from a diesel mechanic, to being recruited, trained and sent around the world as a Marine Special Operations Raider. He served in the first peacetime mission set in Indonesian embassies once combat operations ended in Afghanistan in 2013. That experience motivated Questell to pursue a career change.
“I learned that my younger guys on the team did not own suits,” he says. “They had them, but they fit really poorly and it wasn’t a good representation for our organization.”
Notwithstanding the 1932 Singer sewing machine Questell inherited from a great aunt, he appears (wait for it…) tailor-made for his profession. It’s hard not to miss Questell—dressed in a made-to-measure navy and pale-blue twill striped, European-cut suit with a paisley lining, matching trousers with Italian suspenders, a custom navy striped shirt, a vintage hand-knitted red silk tie and one of his favorite pairs of shoes: oxblood double monk straps. He says people often stop him on the street and ask what he does, to which he smiles and hands them a business card.
Questell wants to inspire his brothers still in the military and show that it’s “not that hard to start your own company.” He went back to school, finished his undergraduate degree and is now engaged to a fellow veteran. They’re planning a June wedding at Keswick Vineyards, where Questell will showcase his work. He’s a strong believer in versatility—that what you wear on perhaps the most photographed day of your life can be worn day-to-day, too.
“How much cooler would it be to get a nice suit that you could get married in, take with you and write your own tailored quest?” Questell asks.
Questell says he doesn’t settle until he gets that “wow” from clients, calling it a game-changer when “guys transform into what they want to be.” He incorporates stylistic elements and materials from his world travels, such as cashmere pashminas he bought in Afghanistan.
Questell focuses on the educational aspects of men’s fashion—modeling his mission to educate and build clients’ confidence in themselves after what he learned in the Marines.
“I take that from my own Special Operations model of train, assist and advise,” he says. “So taking that with style, I’ll teach you the tools to go to your wardrobe, put something together and know that it goes [together].”
Looking to grow his business, Questell now offers clients the opportunity to gift custom tailoring sessions. He has his eye on a showroom space, tapping into the wedding industry and building his sales team.
He doesn’t mind getting several text messages a day from clients or friends asking him how they look—to which Questell responds, “You got it, brother. Keep on.”