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Chicago's Finest: Eneale Pickett

Updated: Mar 15, 2021

There is a poem that I read in my creative writing class called, Soil Horizon by Tiana Clark, where she asks a question about black bodies and the history that comes with them and what has been done to them. It is a question that I have often asked, wondered how I could respond to it, but more importantly it is a question I rarely see getting the answers that it needs. Her question:


“How do we stand on the dead and smile?”


Black bodies have fallen from slave ships, on plantations, during riots, in prisons, into illness and addiction, and from bullets that fire out of guns, and it just seems like they keep on falling. What is the response that we need at a time where action must be demanded? How do we hold others and ourselves accountable without being blinded by the current progression we’ve achieved? How can we bring ourselves back to reality, to a greater sense of consciousness, to affirmatively act to get where we still need to go? I always wonder about what can be done and how I can use my art as a platform to answer those type of questions. Well, there’s someone who is.


Eneale Pickett is a young twenty-two year old revolutionary on the rise who is giving his response to those exact same questions I asked earlier. And I couldn’t see any better way to do it. Through a clothing line called Insert Apparel he is shaking the table bringing the turbulence, demanding change, and giving a response that is needed at a time like this — a response that requires each and everyone of us, regardless of race, gender, socio-economic status, sexuality, political standpoint, or anything else, to place ourselves in conversations that MUST be had despite the fact that it might be uncomfortable.


Currently a Junior at the University of Wisconsin-Madison, Eneale comes from the West Side of Chicago. For most of his life, he lived in an area commonly known as K-Town, where he grew up in the in the Jeffrey Manor projects. Born to teenage parents, his father had him at the young age of 15, but he passed at 17. Loosing his father at a the young age of two, had a heavy influence on the way he creates his art. It instilled in him a constant fear of death and a want to create as much art as he possibly can in his time on this earth. Always unapologetic, Eneale Pickett’s signature work is inspired by being from Chicago which taught him how to be real and un-apologetically himself in each and every situation, equipping him with the tools to attack systems, be bold in the face of white supremacy and adversity, while also doing amazing things “for the culture,” for the everyday people like you and me through artistic activism, poetry, and acting.


The Firstwave Scholar (the only artistic/activism based scholarship on a college campus) from the ninth cohort, is thankful for the amount of resources that he has access to create the art he does. Although the platforms he could’ve used are endless, he chose to focus on fashion. When I asked him why fashion, he responded, “Looking back at movements fashion was a huge contributor to what the movement even looked like. In the 60s you had Martin Luther King Jr. and the Civil Rights activists in suits and business dress clothing. In the 70s you see the panthers in leather, so fashion definitely contributes to culture.” And as a designer it is his aim to create a culture in the fashion world where the people can fight white supremacy without fear, where he can create clothing that speaks “truth to power,” without the people wearing the clothing even opening their mouths. In the creation of a brand it is his focus to make it known where people stand on issues just by his clothing. Which is why in future plans he wants to include notes to buyers, customizing their experience, explaining to them the meaning behind the quote so that they are educated on the meaning, so that they can then internalize it, and then go on to educate others because that is how ideology is spread. Passed through hands through text, passed around in conversations, passing around the information is one of our greatest ways to spread information, even when we don’t have the resources or support to bring attention to it or spread the word on a national or global level. And although this revolution might not be televised, nothing is stopping him.

The first shirt that he released said “Affirmative Action didn’t grant me access to this space,” where he tasked people to write their names inside of a black box at the top (of the shirt) inviting them to insert themselves into the quote. This ultimately became the inspiration for the name of his clothing brand: Insert Apparel. With his work he encourages people to who want to buy one anything he produces to do their research. They don’t have to go extensively look into books and pull out the archives — unless they want to of course. But he encourages his customers to understand the meaning behind the words on his products to understand and look into the topics about social issues and how they impact marginalized groups, while also tasking them to reflect on how they play a role in that impact as well. These are the same he had to do in his process of creation. Every project he releases he dives into extensive research on the topics he wants to focus on for two to three months before even coming up with quotes, designs, materials, or anything else, ensuring that he is looking at his work critically.

Because a lot of his work focuses on systems, he encourages people to also understand those systems and how they work to perpetuate micro-agressions and other isms that exist in this society. And after all that research there is still so much for the 20 year-old college student to learn. In my interview we talked about the concept of “wokeness,” and how in all actuality it doesn’t exist because no one can ever come into full consciousness. He told me that he prefers the term “critically aware” which means that people are critically aware of what is going on surrounding them resulting in them critically thinking and analyzing those things to understand and respond whats going on. One of the most unique things about his brand is that he tasks his customers to also conduct their research in everyday conversations, which can be done by paying attention to the responses they get for wearing clothing from this brand while also the conversations that are sparked from the initial responses or reactions. “That shirt reflects a system that someone is forced to go through everyday. And by wearing that shirt if you want to talk about that system, to try and dismantle it, first you gotta open your mouth,” he said, further encouraging others to utilize themselves to aid in the dismantling of systems that keep so many of us bound daily.

The education major calls his work “academia on a shirt,” seeing that all of his work is inspired by and has been pulled from other academic sources. Every significant person in his life has been a teacher, which has fueled his passion for wanting to educate others to influence and impact the lives of others. He aspires to one day go back to Chicago to teach, being able to transfer the knowledge he gained and implant it back into the communities that he was affected by. He also aims to influence other communities that he never got the chance to infiltrate — and maybe one day hopes to teach classes surrounding his products. Discussing his passion for education led us into talking about the Chicago Public School system, which was interesting be able to talk to someone else about their experiences as a CPS student. He recalled an instance where a teacher told him that if they were black they would’ve gone to college for free. At the time, he was still maturing and growing, and hadn’t came to an understanding of the systematics behind that statement. After graduating high school, coming to Madison created a space for the young activist to grow, mature, and begin to understand the different issues surrounding him in everyday life. The turning point for Eneale was when his cohort sister, Synovia Knox, was spit on by an Asian student telling her that students of color on scholarships didn’t deserve to be here, assuming that she was poor because she was black and on a scholarship. This taught him about anti-blackness, unveiling that it can exist from whiteness, mediated images, and other existing social factors. And instances and experiences like these were a constant reminder of the misconceptions and underlying privileges of racial identities and have all been experiences that have been influential in his passion for his artistic activism.

The artistic goals of his pieces are to provide a sense of racial uplift and pride, to be un-apologetic about the black experience, while also tasking everyday people to insert themselves into complex conversations that are often avoided based on who is comfortable and who isn’t. These conversations force us to stop focusing on emotions and instead direct our attention to critically thinking and understanding the systems that exist around us, and systems that other people must experience daily. The release of his “No Justice” collection was designed specifically for the critical analysis of the criminal justice system and how it has served black people throughout history, including the most recent instances of police brutality. The images he released, specifically the people lying down in black with roses and hoodies, in his video came to him in a dream, he didn’t know what the dream meant, but knew he had to make recreate that imagery into a reality. “Once you add a visual that’s so daring, so intense, it forces you to talk, and say something. Now I have to give attention to this issue because [offending police], to them, is unacceptable. But my body all over social media, dead, is acceptable,” Eneale is a young artist who has taken political propaganda techniques that have been used for centuries to do something to grab everyone’s attention. With bold statements and unique designs placed carefully onto garments, his work is not to be underestimated. He should be valued and must be protected at all costs. His black boy brilliance is incredible, but his message is crucial, his work is priceless, and in all honesty he has has the courage to do something many of us are too scared to do, insert ourselves into the conversation.


If you are interested in staying tuned in to his work, please do, he’s a truly inspiring individual, and the work he’s doing is amazing. Right now he’s working on his Dear Masculinity project, where individuals assigned female at birth, transgender womxn, and gender non-conforming people can submit a letter (300–500 words) to insertapparel@gmail.com by December 14, 2017 on their ideas and experiences with masculinity. In the future, you can continue to look out for a self-care line, so that when you buy a shirt there is a box with lots of awesome tools for you to take care of yourself.


"Those who believe in freedom can not rest."

- Ella Song

Best believe Eneale Pickett is taking no days off, even though he probably should, he is constantly shaking the table, showing the world every single reason why he deserves a seat to eat and satisfy the hunger inside of him for this activism, dismantling of systems, and unconditional love for racial uplift. It was such an honor to be able to interview him, someone who is so young, so influential, so iconic, so revolutionary, the greatest of my time. The conversation was so awesome. Being able to talk about his artist work, but also being able to discuss my own artistic work and being able to be gain wisdom from someone who is already putting in some ground work on issues that are important to me as a designer and activist.

Go and support his work, his message, his medium, and continue to be a source of motivation for a designer who is doing work specifically "for the culture". See how you too can utilize your platform as artists. To close out our interview, we talked about any advice he might give to social activators (not necessarily artists) about utilizing their passions as their platform. He said, "When you face swift criticism keep going. If you are getting criticized that means you're doing something. If you got haters, you doing something right. If you're speaking truth, being real with yourself, you gone make somebody mad. They don't have the bravery to do it themselves, they're intimidated because you were intelligent and brave enough to do what you're doing. So continue doing it."

Those words are something that apply to each and everyone of us and the situations we go through in life. I'm excited to see what is in store for one of Chicago's Finest: Eneale Pickett. Feel free to leave any thoughts on this post in the comments.





P.S. Below is a gallery that you can look at full of Eneale's previous and current work.



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