Categories: Inspiration Style Style Feature

Style Feature: Whitney Middleton

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Photo by Bryan Allen Lamb

One of the best fashion quotes of all time is “Style is a way to say who you are without having to speak.” That is actually more accurate than you imagine. As often times the people whose style you admire most is actually the work of a personal stylist who works with that individual behind the scenes. It is deeper than just pulling clothes and saying this goes well together. It really revolves around getting to know them on and individual level and understanding who they are as a person.

Let’s turn back in time to the end of August and focus on the most recent MTV Video Music Awards. Which celebrity attendee outfit was the most talked about on the runway? It wasn’t Kim and Ye, wasn’t Nicki Minaj, and it wasn’t the fashion icon that is Jaden Smith. It was the man they call Chano aka Chance The Rapper and his wonderful white denim jacket and tan overalls. The visionary behind that outfit was the lovely, Whitney Middleton.

Whitney is a Chicago-based wardrobe stylist who is creating her own wave in the fashion industry.  As the go-to wardrobe stylist for Chance The Rapper and Jamila Woods, she is one of the major influencers in the burgeoning Chicago fashion scene.

Beyond creating a high-impact wardrobe, her background in Marketing, Project Management & Creative Direction ensures every project is executed with the utmost attention to detail. It is that attention to detail which has pushed her to fuel Chicago’s growing cultural development, utilizing her skills for brand development for musicians. Below we talk in-depth with her about her personal inspirations, the Chicago fashion scene, and advice she would offer to an aspiring stylist.

Photo by Kristyna Archer

HFL: Who is Whitney Middleton?

Whitney: I’m a wardrobe stylist, but not in the traditional sense as I’ve specifically focused on supporting musical artists. There’s a huge opportunity to elevate their brand, messaging & music through clothing that most artists don’t have time to focus on. That’s where I step in – to bring their visual appearance to the level of their music, in a way that suits their tastes. My goal and hope is to inspire and elevate their ideas.

HFL: How did you get into becoming a personal stylist?

Whitney: I’ve always loved clothes, but had no idea there was a job in it. My first moment of recognizing I might get to do this work as my career was in watching The Rachel Zoe Project. I saw for the first time what a stylist does and I thought this could be for me. Her business sense and relationships with clients became a model for my career.

The music side goes way-way back. We grew up listening to the good stuff – Zeppelin, Michael Jackson, Hendrix, The BeeGees, Whitney Houston – plus I played in the school band for 9 years. Every time I’d hear a song, I would dream up visuals in my head. A big part of the fun for me was thinking about how I’d dress the cast. We didn’t have cable, so it was my own version of MTV.


HFL: What was that “aha” moment in which you said this is what I want to do for the rest of my life?

Whitney: I was actually in Las Vegas when I realized what I needed to pursue as my life’s work (said no one, ever). A friend hooked me up with tickets to see Macklemore & Ryan Lewis perform on the 4th of July. Mack’s style has always inspired me – “Thrift Shop” may be a goofy track but the first time I heard it I was like, damn. This dude totally gets the feeling of a good find & the power of being a total individual. The energy at their show was insane.

I went out for dinner later that day and wound up wandering into a display of a bunch of Liberace’s costumes. Standing there alone in the beauty of the exhibit, it all sort of clicked for me – I need to dress artists.

HFL: What is your personal style aesthetic?

Whitney: My personal style has changed a lot since I started doing wardrobe full time. I’m always on my feet, walking around, carrying tons of stuff – so it’s become much more functional. I don’t focus much on trends, I really just wear what I feel. I almost always have on at least 1 piece of vintage. I’ve been really into wearing challenging color combos like red & green, midnight blue & black, pink & red. Been into 80’s denim silhouettes that sit high on the waist.

I’d sum it all up as 3 Stacks meets Gwen Stefani/Blondie in the year 2001 with a strong 80’s influence. Makes sense, right?

HFL: Who are three fashion icons that you look up to and have inspired you?

Whitney: Just three? Ha – I have so many! Michael Jackson, Jimmy Hendrix, Blondie, David Bowie, Andre 3000, Kanye West, Rihanna, Macklemore, Gwen Stefani, Liberace. All of them have such deeply unique looks that challenge the norm yet suit them so naturally.


HFL: What is currently your favorite piece in your closet?

Whitney: I’m wearing a pair of midnight blue velvet Doc Martens almost daily right now. Also been carrying an 80’s Gucci bag I got for like $3 in a rummage bin. A pair of high waist pinstripe denim vintage Jordache jeans. Bubblegum pink Vans.

HFL: As a celebrity stylist, how much do you focus on trends to make sure your client’s style is relevant to what we see today while making sure it is still authentic?

Whitney: Like I mentioned, I try not to focus on trends much. To me, the beauty of working with artists is that you get the opportunity to actually create the trends because you’re pulling from their individuality for inspiration. Chance is a perfect example of this. He’s very specific in what he likes & it creates a distinct look that fans can translate and wear because they’re inspired by him. That’s how trends are born.

My first question when I’m dressing someone is “How do you want to look?” We talk about what they’re feeling, the message they want to convey, the event or performance they’ll be at, maybe colors. Then I go to work within those specifications. I’m not about pushing my personal agenda with artists. They trust me to know what’s cool while keeping it super authentic to who they are and what they like. My favorite result of this approach was Jamila Wood’s look for the “Blk Girl Soldier” video. We talked a lot about the message she wanted to send with her appearance for the visual. I had a ton of incredible points of inspiration to work with. That’s the gift of doing this work – being trusted to carefully execute the vision of truly brilliant artists. I’m constantly humbled by it.


HFL: You call Chicago home. What is the fashion scene like in Chicago and its style aesthetic? Do you take pride in the fact that you are helping bring fashion to the forefront of the windy city?

Whitney: Chicago is most definitely my home. One doesn’t immediately correlate Chicago with fashion, but there are many of us out here trying to change that. I’m trying to be the plug for connecting Chicago fashion talent with Chicago artists that are becoming the faces of this art renaissance we’re experiencing.

I think Chicago is still defining its look. I’m actually quite excited to see what develops the more Chicago steps into the art spotlight. It motivates me to work from a place of authenticity when I’m styling because I want to show the vibe here to the rest of the world.

I’m extremely proud to be working in this capacity in Chicago. So many people told me there’s no industry here, there’s no way to make a living off this. Move to New York, move to LA. But I was like…Nah – I’m gonna stay put. I have loved working on the coasts to build my skills set and am so grateful for the opportunity – but my dream is to help create a sustainable industry of professional working artists right here in Chicago. The work we do is important to the overall success & growth of the city, and 100% necessary.

HFL: What are three tips you would give to someone whose dream is to become a professional stylist?

Whitney: First and foremost, anything is possible. I made the jump from financial project management to where I am now in about 4 years. You have to dedicate yourself to this work completely. Take every opportunity as an opportunity to learn & grow. Get comfortable making mistakes because you will make a lot. Learning from those mistakes is the fastest way to get better.

Intern & assist, build your portfolio, take classes – then make it a point to stop working for free. Don’t be scared to ask for appropriate compensation when it’s available. It’s hard to make a living off of art, but it’s possible.

Most of all, be a good person. Listen. Be gracious and patient. Treat everyone with respect. This should be your most important priority not only in this work, but in the world around you.

You can learn more about Whitney and see her full portfolio by checking out her website As well as follower her journey of propelling Chicago’s Fashion and Music scene to the next level by following her @whitney_middleton

Written by: Evan Marshall @Its_what_ev

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