Words: Ernest Wilkins

32-year-old Drew “Drew The Barber” Henderson is so deeply ingrained in Chicago that his No Cuts, No Glory barbershop sits proudly on Chicago Avenue itself. The native Chicagoan has been building a bustling career for years, cutting hair and shaping his clients’ confidence. Along the way, Drew’s become a secret weapon for celebrities from the sports and entertainment worlds, too. And though he isn’t one to brag, let’s put it this way: You could quickly put together an All-Star hoops game consisting solely of his clientele.

With a big-time roster like his, Drew could have chosen to close his doors to the people. However, that kind of thinking is downright offensive to someone who takes such sincere pride in giving back each day. Today, he’s not just an in-demand barber; he’s equally a uniting figure in the community. “I started [cutting hair] at home,” remembers Drew. “My mother cut all of our hair, even my dad’s. She mostly did it to save money, and I have seven siblings, so there were a lot of us.”

Drew’s mother helped instill his creative spirit and hustle. “My mom is handy,” adds Drew. “She can create something really dope out of anything she puts her hands on. I grew up watching that. When I got to seventh grade, that’s when I really fell in love with cutting hair. I still have that feeling, and it’s cool to share that with the community.”

“I wanted to create an atmosphere where people from all walks of life could be themselves.”

If you’ve never had the pleasure of stepping into a quality barbershop, you should know that the environment is everything. “I established the brand to be welcoming for everybody,” explains Drew. “This is a proud city. It can be a little tense. I wanted to create an atmosphere where people from all walks of life could be themselves, feel good and hopefully make some good connections along the way. There are so many different conversations in the barbershop that end up uniting us. Being able to bring together people from different parts of the city is amazing.”

Beyond environment, Drew is no stranger to the power of something that seems so simple, a haircut, and how it can change someone’s entire world —even just for a day. He continues: “Fresh haircut and fresh shoes? It’s over with, man! You have the confidence. In the shop, we see people in all kinds of gear. This is Chicago, being fresh runs through our veins.”

Drew’s contribution to the Jordan Chicago Collaborators’ Collection references his heritage and Chicago’s vastly-underrated transit system. “On the back, those are the old CTA coins,” says Drew, of a graphic on the hoodie and long-sleeve T-shirt, which also tie back to the Brown Line. “Before they had transit cards, there were coins. The coins represent what was going on in 1988, a time when Chicago basketball was great. MJ, of course, was doing his thing. I literally started in my parents basement, so to be doing this now, I feel like it’s proof to anybody here in Chicago that anything’s possible.”


The full Jordan Chicago Collaborators’ Collection releases globally starting February 15.

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