Nike’s black Air Force 1s have always been a staple in Drew Henderson’s wardrobe. They were the shoes he wore in high school and became his go-to for his barber school’s dress code, which required students to wear black shoes.

Now, he’s added another pair to his collection: the ones he designed. Nike recently tapped the West Town barber to design the special edition AF-1 All For 1 – Chicago shoe, which was released December 7 on and in select retailers throughout the city.

The shoe, a variant of the classic Air Force 1s released in 1982, was part of a major project involving Los Angeles, New York, and Chicago. Nike scouted each metropolis for help creating a shoe to represent each city. For example, artist Lauren Halsey’s shoe is inspired by her sculptures as well as colorful posters plastered throughout L.A.; for the New York iteration, the Parks department created a shoe to represent the city’s green and recreational spaces.

Henderson’s shoe? An homage to Chicago’s barbershop community, naturally.

“I personally feel like Chicago has the dopest barbers,” Henderson says. “Chicago just has really good style and we execute it well. We pay attention to detail. A lot of barbers I know are passionate and care about the craft.”

Growing up in Country Club Hills, Henderson’s interest in cutting hair began by watching his mother cut his, his brother’s, and his father’s hair. While studying business management at Olivet Nazarene University, he realized his true passion lay in barbering. He left school after a year to attend Silk N Classy Barber College in Auburn Gresham.

His shop, No Cuts No Glory, originally started in Henderson’s living room, with his first storefront opening four years ago in West Town. The comfortable atmosphere helped the shop evolve into the community hub it is today.

“I try to keep that same presence, like a big living room where people come in and have a good time,” Henderson says. “The guys that I’ve selected to work with me are a group of guys who really care about the craft. They care about their clients and really try to put the same positive energy that I do inside the shop. It’s a place where you can kick back, be yourself, and feel even better about yourself when you walk out.”

Henderson has cultivated a sizable social media following and collaborated with other brands in the past, so it wasn’t a huge shock when a Nike representative contacted him via Instagram last year. Apart from the shoe having to keep its classic black exterior, Henderson was given complete agency in his design.

He laid the groundwork for his shoe by literally starting from the bottom: the checkered outsole dedicated to the barbers who came before him, including his great-grandfather, who came to Chicago from Virginia and spent his life as a barber on the South Side. The green insole represents the color of the first barber chairs Henderson owned. They’re cushioned for barbers who spend all day on their feet and inscribed with qualities he thinks everyone should live by (“commitment,” “respect,” and “discipline,” to name a few).

Chicago’s skyline makes two appearances on the shoe, once on the insole within an outline of two interlocked hands, and again on the tongue, laid atop a hair comb. The back tab is made of pony hair, while the rest of the exterior is made of premium leather with rolled edges. This, along with the wax laces, makes it easy for barbers to wipe off hair shards without them sticking to the materials.

“I’m able to be part of a lot of big projects, but I’m usually in the background. Being the one that everyone is watching on a project of this magnitude, I wanted everyone to enjoy what I created while representing and supporting a lot of people who helped me get to this place today,” Henderson says.

Henderson in a pair of AF-1 All For 1 – Chicagos   Photo: Courtesy of Nike

Nike spokesperson Tim Shaw wrote in an email that feedback on the shoe has been positive, particularly from barbers. He added that Nike was inspired to collaborate with Henderson’s because of his positive attitude and the camaraderie he fosters inside No Cuts No Glory.

“Drew in particular is committed to forging relationships with all of his customers,” Shaw says. “Given our goal of celebrating the individuals and groups that bring people together and move their community forward, Drew was the perfect person.”

Henderson has an eventful month ahead: He’s getting ready to reopen No Cuts No Glory at its new expanded location, 1637 W. Chicago Ave., and on February 15, he’ll celebrate another release for the company’s Jordan brand, the Chicago Collaborators’ Collection for NBA All-Star Weekend. The project tapped Chicago creatives to design apparel using CTA transit line colors to represent an aspect of the city. Other participants include unisex clothing designer Sheila Rashid, artist Cody Hudson, Cole Bennett and Jake “JB” Brode of multimedia company Lyrical Lemonade, and youth empowerment group SocialWorks.

For the series, Henderson contributed a brown hoodie and long-sleeve T-shirt inspired by old transit tokens and the Brown Line. The designs are guided by Henderson’s philosophy that style can add to a person’s confidence and — of course — by a healthy dose of hometown pride.

“There’s a lot of good in Chicago that gets overlooked,” he says. “It was really cool to show that no matter what situation you’re from, the possibility to achieve is there. You just have to work hard and it will eventually find you.”