Chicago native Eneale Pickett awaits challenging conversations with a thick skin and bold attitude. The artist inspires dialogue through his clothing line, Insert Apparel, and multimedia project, “Dear Masculinity.”

“You don’t have to physically open your mouth to let people know you’re speaking truth to power,” he said.

Many people associate Pickett with the viral “All White People Are Racist” hoody, an article of clothing addressing systemic racism but the controversial sweatshirt was not his first time experimenting with fashion.

Before attending the University of Wisconsin-Madison as a First Wave Hip Hop and Urban Arts Learning Scholar, Pickett grew up on the West Side of Chicago, attributing his boldness and ability to stand firm within his beliefs to environment that raised him.

“You can’t be timid in Chicago,” he said. “Sometimes you have to be bigger than life in order to survive.”

Pickett said toning his roughness down in a new environment for the purposes of advancing his academic career felt like he had to police his voice while experiencing oppression. After several incidents of race and bias on campus, he and numerous students had enough.

Pickett participated in a student-led movement in Fall 2015 at the UW-Madison referred to by the hashtag #TheRealUW. He and several other students created a shirt of the school’s beloved mascot in klansgear holding a torch to emphasize the institution’s historical ties with the Ku Klux Klan.

“We definitely expected a lot of people to be angry, but we didn’t expect death threats. I wasn’t expecting the amount of people and level of people talking about it,” #TheRealUW co-organizer Tashiana Lipscomb said.

The shirt meant to shatter an image of an inclusive campus evoked conversations among white students, students of color and administrators. Lipscomb said the conversations surrounding the reality of diversity and equity at the institution continue today.

“From there I saw the power that fashion has to spark a movement. That was our logo,” he said.

The Founding of Insert Apparel

In Spring 2016, Pickett went on to design a shirt stating “affirmative action grants you access to this space” after one of his First Wave cohort members were told they were only at the university because of scholarship and spat on by another student.

“It just sparked something in me because I was able to see my thought process and my feelings on someone else’s body,” Pickett said.

Pickett’s idea to form a clothing line and inevitably create the “All White People Are Racist” including the blood on the sleeves special edition hoody came later that year. He said he wanted to discuss, issues that make people uncomfortable, usually those with privilege.

Through his clothing, he gave voice to people who were marginalized.

“All shirts are poems I could never finish,” he said.
But Pickett stopped making the blood on the sleeves, not just because it was special edition but after one person failed to explain the meaning behind the article of clothing after he jokingly asked what they thought the hoody meant. They replied “all white people are evil” and Pickett said “that’s not what I meant.”

From that day on, he stopped producing the hoody. To this day, Pickett only makes those shirts upon request to people who really understand the meaning of systemic racism and white supremacy.

He then began producing other shirts such as the “Black Boy Brilliance” and “Black Girl Magic” tank tops following the Divine Nine color scheme and “All Men Are Sexist” shirts.

“All men are sexist is true is because I am talking about the systemic oppression that male identifying folks or individuals assigned male at birth inflict upon female identifying folks or people assigned female at birth,” Pickett said.

The Dear Masculinity Project

Pickett began his project “Dear Masculinity,” collecting letters from men of diverse backgrounds, during a time when he began confronting his own masculinity and toxic masculinity within his life.

“I’ve always said toxic masculinity killed my father,” he said.

Pickett’s father died when he was two years old after being shot in a confrontation with a mechanic. From an early age, he witnessed how hypermasculinity makes men irrational and dangerous.

“Toxic masculinity created everything,” he said. “Patriarchy is the main reason for some of the systems we have in place. Capitalism is driven by patriarchy. Racism is driven by patriarchy.”

Pickett wanted to have a conversation about masculinity. He said he wanted an honest answer from male identifying folks as to how they deal with their masculinity.

“When I first thought of [Dear Masculinity], I thought of it as a mini documentary,” Pickett said.

He said this particular project was less confrontational than his previous endeavors but also more inviting. The basis for “Dear Masculinity” was to have a dialogue.

“It was one of the most freeing experiences of my life in terms of really just letting go and feeling okay to let go, to talk about experiences you don’t really talk about,” participant Kenneth Jackson said.

He said sharing his experience will let other men know it’s okay to talk about your masculinity and not conform to the mold of masculinity. Pickett said he hopes men will continue to write letters from every perspective.

“Asking men to write letters to their masculinity is really not going to get anybody up in arms. People are not going to say hang him, you n*****, like they said with “All White People Are Racist.” That wasn’t their attitude toward their masculinity,” Pickett said.

Pickett now records short videos of men reading and explaining their letters to their masculinity every Friday, posting them on Facebook. He said people often wanted to join the conversation, deconstructing their own masculinity and ways toxic masculinity has shown up in their lives.

“I need my homies, my uncles, my friends and even my mother to be like, I get that, that’s something I understand,” Pickett said.