Off The Top | Darryl Brown

By Nick Matthies and Sam Aprile

Darryl Brown is doing it for the “Midwest Kids.” Born and raised in Toledo, Ohio, his design inspirations are rooted in workwear and his Rust Belt childhood. For him, workwear is more than a trend, it’s a familiar and enduring way of life.

Darryl got his start as a stylist working for his friends who played football while he worked full time as a railroad conductor. Chasing his dream of being a full-time stylist, Darryl started working with Machine Gun Kelly, becoming his personal stylist before moving to New York to work with Rocksmith. In 2015, Darryl received a call from Kanye West’s styling team, requesting he come on to work with them for the Yeezy Season 3 show at Madison Square Garden. From there, Darryl joined Kanye’s team full time, becoming Ye’s head stylist. Nearing the end of 2018, Darryl and Kanye went separate ways and Darryl has since started two different labels, “Darryl Brown,” his high-end workwear brand, and “Midwest Kids,” a streetwear brand celebrating kids proud to be from the Midwest.

We sat down with Darryl to talk about growing up in Toledo, working with Kanye West, and what he sees as the future for his two brands.

The following interview has been edited for length and clarity. 

How did growing up in Toledo, Ohio affect your outlook on life, your style, your values, and your work ethic? 

Growing up in Toledo gave me a kind of lifetime underdog mentality. I knew that anything I was going to do was going to be extra hard because I was coming from Toledo. People don’t even know where that is, it’s not even Cleveland, it’s Toledo.

But being from Toledo was also an inspiration. For example, everything I do now—the whole blue-collar, everyday, 9-to-5 workwear mentality, the color tones that I use, the references I use—those things go back to that. I use living in the Midwest as an inspiration.

Being from Toledo also helped me because when I moved to New York, or when I was living in LA, I was used to having to hustle for so much with very few resources. So when I got to New York I was running circles around my friends. It was like when you play a video game and you get to a new level and unlock new stuff, that was how I felt. I was like, “Wow like you guys have so many resources at your disposal, so many ways to help your way of living.” They had a full toolbox and then some and I’m used to coming from Toledo where we don’t have anything. So that helped me take advantage of the resources I had because I was so used to not having those things.

Can you tell us about your initial interest in fashion? How did you decide that being a stylist was what you wanted to pursue as a career?

Growing up, my mom was always pretty dressed up. Even the necklace that I wear, I only wear because my mom had a Gucci Link necklace. She had the big fat one and she would wear all these sweatsuits and had all these rings. I think my first time falling in love with fashion was watching my mom. Deion Sanders was also one of my childhood heroes because I played football and I ran track in high school and he was all about fashion. 

Then when I graduated from college I was trying to figure out my life and a few of my friends from football started to go pro and they told me, “Man you should be a model, you should be a stylist.” I was only 22 and I was like, “What’s a stylist?” They told me what a stylist did and for me, that was really mind-blowing because I didn’t know that was a real job. I didn’t realize people got paid to help other people get dressed. So I started styling all of my friends and all the local rappers. Then I realized I could do this, it came easy for me. 

Tell me about your transition into more serious styling gigs, including Machine Gun Kelly and Kanye?

I was living in Toledo and I met a guy at a streetwear store near The University of Toledo. We set up a meeting and I came on to help him run the store and we started booking concerts and shows. At one point we booked a show at Bowling Green for Wiz Khalifa and MGK before they were big. While we were there I met Wiz and I met MGK. MGK really liked a hoodie I was wearing and he asked me where I got it and what I did. I told him I was a stylist and he invited me onto his team. At this point, he had no style and no status.

At the time, I was just grinding, working for the railroad. I was driving trains and making pretty good money for being 20 or 21 years old. That summer, I started traveling more with Machine Gun Kelly and doing his video shoots and stuff. It was around that time that “Wild Boy” came out and he really started popping off. Things got really serious after that and about that time the brand Rocksmith reached out to me after they saw me putting MGK in their clothes and they were like, “If you ever move to New York we have a job for you here. We want to hire you.” 

And then you moved to New York, right?

I waited about a year and left the railroad to move to New York and work at Rocksmith. I did all of their styling between the end of 2009 and 2015. When I moved to New York that’s when it really shifted. I was just sleeping on couches. Sometimes I would be homeless for a couple of months and I’d just ride the train. I’d be with friends and I’d act like I was going to go home and I’d get on the train and just ride the train all night. I worked for Rocksmith for like 7 years making like $25,000 a year. I literally had to hustle 12 other things at the same time; I had all kinds of side hustles. Every single thing I could think of; styling this guy, styling that guy; Buffalo Exchange; reselling things; anything I could do.

Even though tomorrow isn’t guaranteed, I saw my future at the railroad. I was the youngest guy there by like 13 years and I saw these guys who were older and I could see my future. I’d eventually end up getting married there, having a kid there, settling down there and by the age of 30 I’d be like an old man just thinking about retirement. I know the future isn’t promised but I knew I didn’t want my life to go that way. I wanted better for myself; I wanted different for myself and I was willing to roll the dice. I felt like I maxed out being normal. I had bigger dreams and aspirations so I moved to New York. My parents were disappointed, they thought I was throwing my life away but I just took a gamble and it worked out.

Talk to me about Kanye and your working relationship with him?

It was really a full-circle moment. MGK was living in LA and he was having a conversation with one of Kanye’s styling assistants before the Yeezy Season 3 Show / “The Life Of Pablo” listening party at Madison Square Garden. She told him that they were doing this huge show and they needed help but that she didn’t know anybody in New York. MGK told her she needed to reach out to me and gave her my info. So they connected with me and brought me in for that show so I did a week for them, it was amazing, and then I don’t hear anything for like five months. 

Then I got an email from Kanye’s stylist at the time letting me know they had a position working with Kanye that they thought would be perfect for me. So they had me meet them at this apartment in New York. I met with him and got to work immediately. I went on the Pablo Tour with him and started that whole process and after the tour ended he just kept me on. We really got to know each other quite a bit, each other’s styles, our walks, and our backgrounds. I’m a Cancer, he’s a Gemini, we’re both from the Midwest; we had a lot in common. So we moved back to LA and I started with him full-time and when he and his main stylist parted ways, he moved me up to be his main guy. I was with him until December of 2018 when we parted ways on good terms so I could focus on my brand stuff.

Would you tell us about Daryl Brown, your namesake brand?

I launched my namesake brand, Darryl Brown, this past January in Paris for Fashion Week and the brand is run by me and my fiancé. Over the years I’ve traveled and shopped all over the world and it got to a point where I’d go into a store and find nothing and it started to become a hassle. I thought to myself, maybe I should just start making my own clothes because I’m going into stores to buy stuff for Kanye and not finding what I’m looking for. Kanye actually started helping me; he was like, “Why aren’t we just making the stuff? We don’t need to go buy it. Let’s just make our own.” So I did that with him for a year and then styling with him for 3 years; it just elevated to where he was getting the pieces made and I was seeing this and creating pieces with him. Kanye really breathed confidence into me, like I can really make clothes. I can learn the process here and make clothes and it’ll work. 

So I launched my brand and it’s just my take on workwear, which I think is interesting because workwear has become such a trend and these brands are doing it all wrong. At the end of the day, workwear is just a trend for them but for me it’s my natural being. That’s where I’m from; I’m from the Midwest; I really lived it. I did the 9-to-5 factory life. I really wore these pieces every day. My dad actually wore these pieces, my mom actually wore these pieces. I’m a big fan of Dickies and Carhartt. I love all of these heritage brands and their message and I’m going to capture the hard structure of these lifetime legacy brands but I’m going to message it with the elegance and quality of a Dries Van Noten. I love the elegance that he captures in every piece and I’m going to do that with Darryl Brown but make it workwear inspired. 

What about your other brand, Midwest Kids? 

Midwest Kids is my favorite brand. I created it because when I started doing Darryl Brown I realized that will take a lot of money and structure and I’m not a big fan of the fashion calendar. I needed something to feed my creativity on a day-to-day basis or I’d go crazy. So in 2018, I was wearing a vintage Brown University hoodie and I was telling my friend about how I was sad that my hoodie was falling apart. He told me to just go make my own and I thought “yeah, but I’m gonna put ‘Midwest Kids’ on it.” It just came out so naturally so I made six for myself and was wearing them all of December 2018, rotating them out, and it instantly gained traction. I had a ton of people asking me where they could get one.

I made the brand and got serious about it because I’d be traveling and everyone else was from the East Coast or West Coast or down South. When I’d say I was from the Midwest, they’d act like it was like a third-world country and I felt like we needed something with a sense of pride. A way to declare that we’re from the midwest. I feel like there’s no expiration date on it, I feel like it’s a 20-year brand. I feel like it’s something people are going to be able to wear over and over again for years. I’ll be keeping the collegiate aspect and inspiration forever.

How did LeBron wearing it happen?

What happened with LeBron was crazy because they reached out to me for a hoodie. I’m close with that group and his stylist so they reached out to me and asked for the hoodie he saw me wearing. It was then that I had my friend make a website and put a hoodie up just to see how it did. I sold like 200 in a day and I was like, “Okay. Yeah, this is real.” Then on New Year’s Eve, my phone starts blowing up because LeBron is wearing the hoodie to his birthday party. He did it on his own too, no stylist. He just grabbed it and threw it on and one of his friends took a picture and posted it online. Literally the next day I went and trademarked everything. After that, I sent one to Kanye and that man wore it the same day. From there, it was ball game. 

What would you tell that kid who’s from the Midwest and has similar ambitions?

There’s no right or wrong way to go about it. The most power you have is to be 100% yourself, 24 hours a day. If you really want something just go for it, be yourself, and be prepared to go into the storm. If you’re being yourself no one can ever take that from you.