Designing for Decades

In a time when nondescript sites like Shein and TikTok Shop have made fast fashion more ubiquitous than ever, Tulsa-based designer David Caldwell is pushing against the trend and reaching back into the wardrobe to reimagine an old staple: the leather jacket.

As someone drawn to the meaning behind making, leather makes sense for Caldwell. “Leather is timeless, classic, elevated,” he explains. “There’s always a story behind a leather jacket, no matter where it’s from.”

It’s a proven formula, but Caldwell finds ways to innovate. His work is about longevity: What kind of design will look as good in 30 years as it does today? What’s the most beautiful thing we can make with the smallest amount of waste? At the heart of his ethos is an appreciation for things that last — heirlooms meant to be savored, preserved and passed on.

Though just a year into his current collection, Caldwell has spent decades designing. Fascinated by fashion from a young age (he was the kid in a suit on school picture day) he spent his teen years flipping through issues of Vogue and Cosmo, transfixed by the models and clean lines in the clothing. But despite the interest in fashion, Caldwell pursued a degree in architecture.

At OU, Caldwell drew inspiration from the inventive works of famed Oklahoma architect Bruce Goff, until a study abroad experience in Italy gave him a firsthand introduction to the fashionable world he’d only read about in magazines — one where style was central, and everyone from children to grandparents took dressing seriously. The experience inspired him to start making hats out of old sweaters, and awakened curiosity about fashion design. He eventually transferred to Oklahoma State University’s design program, and after graduation moved to New York to work as an unpaid intern in a coveted role at the buzzy Zac Posen label.

“It was very much like The Devil Wears Prada,” he recalls. “No one was allowed to be around Anna [Wintour]!”

Caldwell spent his days working on a line of vinyl pieces for Posen’s 2009 collection, hand-cutting flowers and leopards out of vinyl with an X-acto knife, hoping Wintour would greenlight something for the collection. “I think she nixed most of the vinyl,” he says with a laugh, “but it was still fun to work on.”

He kept at it for a while, and even made an appearance on Bravo’s “The Fashion Show” (the network’s precursor to “Project Runway”). But eventually life caught up, and designing and sewing fell by the wayside. Years later, Caldwell started working at Black Optical in Tulsa, inspired to be in fashion and styling again, albeit from a different angle. When a buying trip to Paris came up, he felt the familiar itch to create.

“I knew I needed to make some garments for myself to wear,” he says almost too casually — as if anyone headed to Paris could simply hand-stitch the perfect looks for the trip. “I hadn’t sewn in 10 years, but I made myself two jackets and a pair of jeans to wear around, and it reinvigorated my love of sewing.”

After the trip, he went to Tandy Leather in Tulsa and bought a hide, made a shirt pattern and hand-stitched his first jacket. He called it The Heirloom Jacket, and it would become the anchor of his collection. The Heirloom is a stunning leather utility jacket, tailored with saddle-stitching (criss-crossing needles of waxed thread through hand-punched holes) and hand-sewn pockets — it was a time-intensive piece well worth its construction. Caldwell started wearing it around town, folks caught a glimpse, inquiries streamed in and a business was born.

2024 brought noteworthy commissions and partnerships. Caldwell’s designs even found their way to the red carpet, when he created a custom leather suit jacket for director and “Reservation Dogs” creator Sterlin Harjo to wear at the Emmys. Harjo wanted something classic to pair with a Nick Fouquet fedora. Caldwell landed on a lambskin tuxedo jacket with a black calf hair lapel, “to give it that pop and sheen so it’d really glow under the light.”

Other notable Caldwell jacket owners include actor Ethan Hawke, who received an Heirloom jacket as a “Welcome to Tulsa” gift from Harjo, Eric Edelstein and Daniel “Danny Boy” O’Connor, member of hip-hop group House of Pain and Executive Director of The Outsiders House in Tulsa.

Like many of Caldwell’s clients, O’Connor had leaned on him as a stylist at Black Optical for years, and was eager to get his hands on an Heirloom jacket of his own.

“I think he does the utilitarian stuff best — a vintage chore coat or the prism jackets like we used to wear in the ’90s, in these rustic earth tone colors and muted pastels,” O’Connor says.

“I know he likes to find two hides of a weird color to work with, maybe a moss green color that’s not commercially available. He is so good at repurposing, taking oddball things and turning them into high-end, utilitarian vibes. I think that’s where his genius is: taking a practical design aesthetic from the past and making it look very functional and high-end, very ‘of the future.’”

O’Connor, spotted around town almost exclusively in a hoodie, commissioned Caldwell to create a special leather hooded jacket for him to wear to the premiere of The Outsiders musical on Broadway in New York City. The result was a retro, ’90s-era oversized hoodie, which O’Connor describes as having a bit of a “Greaser” feel to it. The design can now be purchased at The Outsiders Museum in Tulsa.

O’Connor said Caldwell’s talent is rare; the sort of thing that’s hard to find away from the coasts.

“Coincidentally enough,” he says, “I grew up around Richard Stark and Henry Duarte,” two notable L.A.-based designers known for leather making and suits. “David reminded me a bit of them. To have come here and found something like that in Tulsa in 2025 was incredible. You hold it in your hands and you can just feel that it’s worth it.”

“It was very much like The Devil Wears Prada. No one was allowed to be around Anna [Wintour]!” –David Caldwell

While Caldwell understands that a leather jacket is an investment, he doesn’t worry about fast fashion erasing demand for real, premium heirlooms.

“Leather will always hold its place in culture,” he says. “There’s a lot of non-leather options that give it that same look, but I think leather will always have the touch, and the smell, and a way of transporting you through time. It can take you to another place.”

Caldwell is currently at work on a few new styles that he’ll debut at Abersons in Tulsa on April 17, from a biker jacket to a bomber to a varsity jacket, and even a trench. And of course, the Heirloom.

Making jackets by hand is time-intensive, so Caldwell is looking for a production partner who can help him scale his inventory. But even as the business grows, Caldwell wants to keep the operation small, mostly commission-based, so he can continue to sustain the custom details that make his pieces one of a kind. For instance, the laser-etched personal touches he leaves on the inside pocket of each customer’s jacket — perhaps a saying, a birthdate, or in Harjo’s case, a photo from the show. It’s the kind of thing that takes time and care, but will never lose its meaning; a one-of-a-kind heirloom made to be preserved.

“Leather’s meant to last a lifetime,” Caldwell says. “I want you to buy one piece that’s going to stand out in your wardrobe and last forever.”