When Jennifer Lopez momentarily halted Earth’s orbit with a certain plunging down-to-there Versace dress in 2000 (subsequently inciting the launch of Google Images), the creative mastermind behind the look was left unnamed and uncredited to the public. Of course, fashion insiders knew that then-stylist Andrea Lieberman was responsible for many of the superstar’s early aughts looks that have informed and shaped culture, including that Grammy’s red carpet stunner. From that moment, a wave started building into a seismic industry of stylists and wardrobe creatives who not only have more influence than ever, they have their own followings. Enter the age of the image architect, and one of its most formidable players: Matthew Henson.

If you or your wardrobe have felt the influence of streetwear, it’s at least partially due to Henson, whose high-end, lowkey aesthetic has infiltrated Instagram feeds and city sidewalks worldwide. From hip-hop icons like The Weeknd and Kid Cudi, to up-and-coming actors like Charlie Plummer, his clientele covers a large cultural surface area. Most notable of his superstar collaborations is with A$AP Rocky, with whom Henson also helped form the creative collective AWGE. Before entering the styling arena, Henson served as a fashion editor for Complex, where he first met Rocky.

What sets Henson apart from others of his cadre is his portfolio: He’s a man who styles men, and was one of the first stylists to create wardrobes for his clients rather than fitting them into a mold set aside for male celebrities (though he admits there is a secret sauce to what he does). I sat down with the New Jersey native at Freds Downtown to talk about styling, shopping, and his hidden talents.

RICK OWENS Colorblocked Mohair-Blend Crewneck Sweater

Noah Silverstein: Where did your appreciation for fashion originate?
Matthew Henson:
My maternal grandfather was a business owner and both of my parents worked in the medical field, so they all were very well dressed at all times. My dad always had his pants creased and starched, everything always dry cleaned, and my mother was always very fashion conscious. I think that really had a big impact on me—even though I do not get as dressed up, even as an adult. My style is very relaxed.

How did you start to develop your own relationship with clothes and style?
I had a full-time job during college in hospitality, and I would always take a lot of creative freedom in the way I would dress up our uniform, which was a light brown canvas suit. I would wear colorful shirts underneath or my shoes would be outlandish—just ways to separate myself from everyone else. I eventually found a magazine internship through a friend and when an assistant job became available I started working my way up through the ranks to become a fashion editor. It was really tough and fast-paced, but the things that I learned set me up to move on to Complex, which at the time still had a print component and gave me the opportunity to focus on menswear, which was and still is my passion.

How did the jump into styling happen?
At the time, the men’s industry hadn’t hit the boom that it has now. I met Kid Cudi early on in my career, and he was amazing. He had an album coming out and there was so much press about it and had so many red carpets and I worked with him. I try to go back and look for those images and I can’t find them, it was a pre-having-your-iPhone-out world. There were so many looks that we did that are, like, legendary and amazing and you can’t see them anymore. Then at Complex, I met Rocky.

RICK OWENS Cotton Oversized T-Shirt / Colorblocked Mohair-Blend Crewneck Sweater / Karloff Cotton Boxing Shorts

What was that meeting like?
We didn’t necessarily click, but I think working together over time on different projects with him we definitely found a great rapport and a working process that has brought us to where we are today.

How do you decide who you want to work with?
For me, it’s been the universe working in my favor and the right people coming to me. A lot of people do reach out, but for me it’s not just a job and work and having this roster of like 15 people. I really like to enjoy the people and the artistry I am working with, so if you’re a musician and I think your music is shit, it doesn’t really make a difference to me whether you can pay my rate, it’s about a genuine connection because I build off of your artistry and it is an extension of that.

What’s the beginning of the process like when you start working with a new client?
It’s 100% different for every client because everyone has different tastes and interests. Some people care more about clothes than others. I’ll go in and they’ll be like “this is great,” and I’ll put it all together and they’ll wear it. Some people have their own personal styles so you can’t tell them what to wear, you have to build it with them. That dynamic is really beneficial, when you have an idea and they have an idea and this idea comes together and it’s like this great Instagram breaking moment—whether people like it or not, those are the really rewarding moments.

RICK OWENS Plaid Wool Coach’s Jacket 

Is there a notable moment you can recall from working with someone new?
I work with this young actor who is very talented named Charlie Plummer, he’s in a new series called Looking for Alaska, which is coming out on Netflix. I wanted him to wear this pinstriped Loewe suit from the runway, and I guess it was slightly in high demand and everyone wanted to wear it. We didn’t have a fitting before and I literally had 45 minutes with him from walking in his house, getting him dressed, and leaving out the door because he had just landed from filming. He tried on the suit and it looked immaculate. He literally put it on and walked out the door. It was amazing.

As someone who works with clothes everyday, do you like to shop?
I have an issue with shopping because I dress very simple. I love dark colors, and whenever I’m not wearing them, it’s me experimenting with something in my head and trying things out on myself that I want to perfect on other people. So my closet isn’t really a reflection of me, it’s an archive of things that I want to collect, things that I want to try, and then just a whole bunch of black and white things that I wear on a daily basis.

RICK OWENS Cotton Oversized T-Shirt / Colorblocked Mohair-Blend Crewneck Sweater / Satin Wide-Leg Tear-Away Jogger Pants

Tell me about what you’re wearing today.
I love Rick Owens, I’ve started collecting pieces from him and other designers over the years. But I really love the way Rick dresses.

What do you think is the next evolution of your career?
I have been thinking about ideas on how to approach retail. I think as someone that not only pulls from brands but is also a big shopper, I do love the stores and the experience of shopping, but I also think there is a big disconnect with how modern people consume things. A lot of people aren’t coming into the store and buying the whole collection, most people just want to come in and buy some really great pieces to add to their ongoing wardrobe. With there being so much clothes and so much noise in the space, it is hard for people to decipher what they want and what they need, and that’s something I think about all the time when it comes to retail. How can we change that?

Do you have any hidden talents we should know about?
My hidden talent is probably being able to make people laugh. Also, and this is no joke, I can actually really sing! It’s crazy how I don’t have an album. It’s actually like I’m hiding something from the world.

RICK OWENS Leather Shirt Jacket / Cotton Oversized T-Shirt / Colorblocked Mohair-Blend Crewneck Sweater