ComplexCon 2024 Brands to Watch

As much as we all wish we could, we can’t always afford our favorite luxury pieces. That conundrum is what inspired Jackson Napier to pursue clothing design as a high school student in Georgetown, Kentucky over a decade ago.

“I was like, ‘Why don’t I try to make my own clothes so I can dress the way I want for cheaper?’” Napier tells Complex.

The decision proved to be the right move. Napier has found his niche by giving approachable staples like hoodies and cargo pants an avant-garde twist. The results are items that perfectly toe the line between streetwear and luxury, making Napier one of the most promising young designers to come out of Chicago right now.

The 27-year-old taught himself garment construction and patternmaking by reading books and watching YouTube tutorials. He would take apart clothing items and put them back together using a sewing machine that he kept at the foot of his bed. When he finally designed his first piece in 2018—a canvas crossbody bag—he was an undergrad at the School of the Art Institute of Chicago.

Moving from a small city in Kentucky to a metropolis like Chicago allowed Napier to learn more about the world of fashion firsthand. He visited Notre and SVRN, two popular clothing boutiques in the city, to touch and feel garments from brands like Rick Owens and see how they are constructed. Seeing the success of fellow local designer and Brands to Watch alum Kristopher Kites also gave him the confidence to pursue his own endeavor more seriously.

“It was inspiring. It showed me that it’s possible,” says Napier.

The Armadillo Pants are one of Jackson Napier’s strongest offerings. via Jackson Napier

He designs an array of items from jackets, hoodies, and caps to handbags. Pants are his strongest offerings. His Armadillo Denim is a pair of cargo pants with panels and rounded legs that resemble the creature’s leathery shell. Other styles reference his previous work, like the military-style Convertible Cargos that are a maximized version of one of his earliest Pull Cargos. They feature deep, scooped pockets and exaggerated leg straps that the wearer can customize to their liking.

Some of Napier’s other standout pieces are the Traveler’s Cap, his unique take on a du-rag, complete with a brim and long ties, and the Nomad Hoodie, which features an X-shaped harness across the front and back that can be used for storage. Everything is meant to mix style with functionality.

A majority of Napier’s designs are sold in neutral tones like black, white, and gray. Occasional pops of color come in the form of red caps or lime green bags. One thing Napier has stayed away from thus far is graphics—despite his artistic background, don’t expect to see paintings on his clothes any time soon.

“[That’s] something I pride myself on,” says Napier. “It’s harder to sell a garment or create something that people are attracted to just off shape and color alone.”

Drops are kept fairly limited, with only 50 to 100 pieces per SKU. Eventually, Napier hopes to produce full, seasonal collections and show in New York or Paris as part of the official Fashion Week calendar. He also wants to continue expanding his network of collaborative partners. He’s already worked with Utah’s Badson on versions of the Traveler’s Cap and Convertible Cargos, as well as Chicago-based jewelry designer Olivia Nash to create his signature Flower Bag. Bubble coats and womenswear are some categories he wants to tackle next.

Napier’s steady rise wasn’t without growing pains. In August 2023, he took to X to address Drake’s stylist Drew Ferguson for not paying him for a custom pair of leather Armadillo pants that he made in just 48 hours. Napier got paid shortly after his posts gained some traction, but that wasn’t the only time he had compensation issues when working for a famous client. These experiences have caused Napier to de-emphasize co-signs from celebrities, even though they can be beneficial for an emerging designer.

“It’s always last-minute. It’s always for free, or little to no money,” says Napier. “I understand why it would be good for the brand, but I try not to prioritize it or think about it too hard just because of the situations I’ve been in.”

For his Brands to Watch booth at ComplexCon 2024, Napier will sell pairs of his Armadillos and Convertible Cargos, as well as Traveler’s Caps and Nomad Hoodies in a variety of colorways. Most pieces will range between $60 to $250, with special one-of-one leather jackets priced at around $400.

“You don’t need to have a name brand or a logo on to stand out. Seeing the joy when someone wears something I make and feeling confident about themselves, that’s what really inspires me,” says Napier. “I want people to leave my booth with a full outfit.”