“If you build it, they will come.” The quote might be from “Feld of Dreams,” but it’s also the way Chicago fashion stylist Whitney Middletown views her beloved hometown’s growing art scene. Known for working with some of the city’s most noteworthy musical artists including Jamila Woods and most notably Chance the Rapper, Whitney is on the cutting edge of the city’s culture, changing the art world from within.
A former banker, Whitney left her job behind and followed her passion for fashion, leading her to style for New York Fashion Week and the cover of Billboard Magazine. A graduate of the University of Illinois, Whitney holds the city close to her heart, styling for a community of some of the country’s top musical artists and making the city a hotbed for arts and culture. Whitney draws her style from almost everything around her—a self-described sponge of fashion—something she incorporates into every one of her style sessions.
I spoke with Whitney about Chicago’s growing arts scene, being a celebrity stylist and working with Chance the Rapper.
Could you tell me a little bit about what you do as a professional stylist?
I’m a wardrobe stylist in the traditional sense of basically going out and pulling wardrobe for clients for shoots and doing some work for e-commerce-type platforms.
But, I have a niche in working with music artists. So, that’s a little more comprehensive—it kind of combines all those worlds. It’s thinking about the sound of their music, the tone, the message of their music and then translating that into their wardrobe. It’s a really kind of thoughtful process that’s less based on trends and more based on what the artist wants to express. I played music growing up. I was in the band—I was a band nerd—and always loved it. I was raised on classic rock and my brother loved hip-hop, so I grew up hearing all of that.
This job really helps me combine my love of fashion and music. Musical artists are just so exciting to work with because they just love to get a little more creative and wild, than—say—an editorial of a model for a fashion magazine that’s based on trends and selling for sponsors and all that. It’s really a creative, free space. Starting at the artist level and working on them with wardrobe is kind of one of the birthplaces of trends. So, it’s pretty cool being on the bleeding edge of that.
You used to work in finance, but discovered your passion for styling. When you started styling, you would offer free services to artists and tried to just help out in any way that you could to get involved in this industry. What was the thought process behind starting that and why did you make that transition?
I knew I always wanted to do something in fashion and be more creative. So while I was still working in the finance world, I was just doing stuff like blogging and getting a photo portfolio together so if someone looked me up, they would see that I wasn’t just like a finance person—I had a creative side too.
I wasn’t sure how I wanted to style, but someone asked me who I liked and whose style I thought was cool and I mentioned Macklemore and Ryan Lewis—I think they just have the craziest style. So they were like, “Oh, you should go to he’s playing in Vegas.” So I ended up getting this really special experience, getting to see them and meet them.
That night, I stumbled upon this Liberace exhibit. And obviously, he’s famous for his costumes and I just had one of those light bulb moments where I was like, “Okay, I need to do this in the music realm. This is my niche. This is where I need to go.” So I just started going to shows and finding artists who I liked their sound and thought were cool ad had something interesting about them already. That’s when I started doing the reach out and was doing everything for free—helping them shop, and all that.
Then I got connected to this music photographer who booked me on a shoot with Chance [The Rapper] for STATUS magazine in February 2015. When I was doing the pull for that, I actually heard that he was headlining Pitchfork and I made a mental note like, “Alright, I’m gonna reach out again. If this goes well, then I’m gonna check back in on that and see if they need help.” And that’s what I did, and they did need help. So, when I was there, I met Jamila Woods, who I work with very closely now.
Just starting from that platform and getting to work on a show of that caliber right away was kind of like, “Here’s your wildest dreams in front of you. Now try to figure out how to do this more.” It all kind of started on that shoot. Really, connecting the dots has been the most important part of trying to figure out what’s a natural progression and developing my eye and my style and being in line with artists in the genre and that field has also been really helpful.
A lot of people don’t often have that drive where they can just stop doing a job they don’t love and strive for something they love. What gave you the courage to just stop your finance job and pickup this whole new career?
It really stemmed from a general dissatisfaction of the majority of how I was spending my days. I really felt like I was two people. I was one person when I was in the finance job—obviously it’s a very world. And then I was another person when I was getting home at night—like my real self or closer to my real self. That was really difficult and unpleasant. I was just like, “I need to think of a way to be myself and do what I like and be able to make that a career.” It kind of started on that pursuit of happiness point of just trying to find a way to enjoy the work so it doesn’t feel like work. That’s how I got inspired to move forward. I also was a marketing business major at the University of Illinois, so I still use that. That’s a very useful degree, but the finance stuff—I just couldn’t live in spreadsheets.
So, I took a course at FIT and worked six seasons as a dresser at fashion week [in New York]. It was all pro-bono—like working the lowest level in the thick of it—but you get these amazing experiences with the best designers in the world. It helped me move from working at a bank to working at eDrop-Off luxury consignment spot, and doing their windows and social media and web content for photos and styling. It really helped me build my core base before I was able to go out on my own.
Obviously there’s a huge fashion industry in New York and LA, but you have the “Field of Dreams” philosophy of ‘If you build it, they will come’ talking about Chicago arts and culture. Why do you feel this dedication to Chicago, rather than heading to one of these huge fashion capitals?
I think the coasts are amazing. Obviously, there’s such a huge industry in New York. I’ve gained so much from working in New York and there’s a lot to respect about what they do there. But, Chicago has kind of been waiting for its moment, and I feel like there’s this perfect storm of people here right now who are just like, “Okay, I’m not just gonna build my portfolio in Chicago and use that to get a job somewhere else.” I think it’s such a life goal and a cool thing to be able to put in the extra work and figure out how to team up together here and sort of build what we want the future of art in Chicago to be. Going to New York and going to LA, you really don’t get that opportunity to start something new because it’s so saturated and so expensive. There are already so many establishments out there running well and doing it right.
I just think it would be a beautiful thing to stay here and really commit to the city and utilize resources on the coasts, but ultimately make the investment in Chicago. Nobody can do it alone. You really have to work your connections and find your tribe. In this city, there are so many great groups of people that come together. The ‘60s in London is sort of the model I look to because when the rock n’ roll scene was really building there, it took the fashion work, the art world, the photography world with it, because those artists need all those components to be stars. And I think we have that here. There are so many incredible artists who are kind of leading the charge here for the rest of us to figure out ways to help them out and get them to the next level.
What do you see for the arts community in Chicago over the next couple of years. There’s obviously been a lot of movement in not only the arts scene, but the culinary world, startups and definitely the music scene.
What I see that we don’t have is a good infrastructure to support artist to work regularly, and be able to support themselves financially in Chicago—specifically speaking to the fashion world and my world of styling. In New York and LA, you have things like showrooms that are these big huge warehouses that hold all these different collections. The PR firm that runs it acts as the liaison between the stylists and designers. So as a stylist, you can go in there and be like, “I need a red ball gown,” and you can just go to this place and see a bunch of different collections.
We don’t really have that here, so it takes going through like 10 different spots to pull for a shoot. And that’s super discouraging for a stylist, because it makes pull days that much harder. But, getting those types of things in place and attracting designers and supporting designers that are already here to get together to pull their resources to not only make it easier for them to distribute their line, but for stylists to pull from their line for an artist to come in and shop directly from their showroom. That’s definitely what we’re missing.
The more that people like myself and others stick here and hold our ground and look to the coasts as the models for how we can get started and actually build that is going to be the next step. So, actually building that is going to be the next step. I sort of see more of a formal infrastructure that’s going to attract more talent from outside Chicago and keep the talent that’s already here.
You mentioned reaching out to artists with a distinct message in their music inspires your styling work. What draws you to an artist that makes you want to style for them?
Jamila, particularly, is someone who has such a strong voice in the activist community here in Chicago and uses her music to speak to some of her personal struggles. I think Chicago is really the center of the civil rights movement in America right now, being that we’re such a divided city and everything that’s such a terrible struggle here with people in our own city. She really has a platform to use her music to give a voice to some of the people who are working really hard in the activist community. She did this incredible panel when Macklemore’s tour came through—she did the song “White Privilege II” with him—and the draw was him being the face, but it was supposed to be a bait and switch to get members of the white community out and get members of the black community out and speak to everyone about ways to be an ally as a white person that aids the movement rather than inhibits it.
I’m getting off topic, but all that messaging and hearing it directly from Jamila is just so inspiring to me to work from a place of such importance and struggle and hope. It really brings forth the best source of inspiration to take her vision and what she wants to say with these really powerful songs and create wardrobe that really speaks to it without overpowering it. It’s a really special position to be in and one I don’t take lightly. I just feel incredibly honored to have that relationship with her and to help her push the messages she’s looking to push.
What influences your style on a daily basis?
I feel like I’m kind of a person who is sort of like a sponge for things. If I spend a lot of time around a color palette or I’m watching a certain movie or type of music, it tends to trickle in subconsciously to how I express myself with clothes. I’m really inspired by the artists I work with. Although, I don’t want to dress exactly like them, but it does happen a little bit sometimes.
Growing up, my maternal grandmother was like the style icon. She was big on garage sales and shopping and taught me a ton about that, as did my mom. My mom was like the modern day shopping education for me, and my grandma was like the vintage education. So, I wear a ton of vintage. I love finding a piece and making it modern and trying to mix it with modern clothes. I was wearing a lot of black for a while, but I do love colors. I love Jeremy Scott, too. I’ve been watching this documentary on him—I’ve probably watched it five times—and I’ve noticed these pinks and lime greens trickling into my palette. So, I pretty much soak up whatever’s around me and let that dictate whatever I’m wearing.
Similar to your “Field of Dreams” philosophy, Chance the Rapper is really the new poster boy for Chicago. You started working with him just as his star really started to blow up. What has it been like styling for an artist that is getting so much attention and is so in the spotlight?
It’s so amazing. I love the independent spirit behind everything that he and his team does. Obviously, he is a brilliantly gifted artist and he has such a wonderful message of positivity and togetherness and growth and support behind him, which is a really appealing message for the world we live in today. It’s not about appealing to people, that’s just authentically who he is. Record labels are quaking in their boots—as they should be. They’ve been using a model for years that I really disagree with, in a sense that they sign an artist and manipulate them to make sales and make money, rather than support their art and their unique voices.
That’s why I admire the Macklemore team so much, because they’re independent and really went against the record label because they were so disgusted by how little a voice artists actually get and how much it limits the true art and burns people out. I think they were really the first to show that indie artists have a voice. They took home the Grammy and had huge hits.
But now, Chance is really the new model and the bigger model of how to do it. He’s created a business to support his art and he knows his fans and loves his fans. It’s just this beautiful example of letting the artist be the artist and letting them take the lead on their creative vision and letting them take the time to put out music in a way that makes sense. It seems like “Duh, of course.” But, if you give your music for free and build a fan base who can access it whenever they want, of course they’re going to support your work and come to your shows and want to look like you and purchase merchandise. Everything he does is just so brilliant and I’m always so blown away by it.
It’s been incredible to watch each step up close. He’s basically changed the rules of the Grammys and now he’s onto hip-hop radio to change that infrastructure. He’s totally inspiring all of these artists who have felt mistreated and haven’t been giving the proper chance to really express themselves. He’s showing people it can be done without having somebody puppeting their career. One of the coolest parts about working with him has just being able to see how much he’s inspiring other artists to take steps to be authentic and make their art from a place that feels true to themselves.
I’m sure you can really relate to that mentality, starting completely on your own and building up this styling career that has led to these high-fashion shoots and magazine covers. Do you ever think about where you started compared to the success you have today?
I’m not really a person who sits and digests it a whole lot. It’s rare that I’ll take time to stop and sit on it. But, obviously there were so many people that have helped push me forward. I have a great agent who has helped manage my commercial and fashion bookings—David Sanchez. And even working for eDrop-Off, taking a chance on this banker who kind of wears these cool clothes and pushing me even when I was scared and wasn’t sure if this career was a possibility.
I just feel really grateful to have these amazing platforms to also kind of integrate some of my thoughts in my art. That’s the coolest thing—just having a space to create work that people see, especially working with artists that people love so deeply and that inspire me so much. It’s hard to even think about it sometimes, like “How did I even get here?”