What should I wear to prison? Does it matter?

I spent a lot of time thinking about what I should wear to prison.

I’d just been granted the rare opportunity to visit six prisons throughout the U.S. to interview participants of an educational program as part of a program evaluation I was conducting for a non-profit I’ve worked with for a number of years. A camera crew would join me to document the interviews that I was recording on my hand-held device. 

The organization, World Impact, Inc., offers a 4-year theological training program (called The Urban Ministry Institute, or TUMI) that equips men and women to be pastors in their community—men and women who might not otherwise be able to complete a college seminary degree due to financial, time, or entrance constraints. In addition to offering the training program to men and women in communities of poverty, TUMI is also available inside 68 correctional facilities throughout the United States.

I had been given access to a place where few people are allowed to go, and I didn’t want to blow the opportunity. I’d traveled over 1500 miles, filled out the necessary paperwork, and had been granted clearance to enter three prisons in the Houston, Texas area and three near Wichita, Kansas. There wouldn’t be another chance to get this right.

A lot was riding on my appearance.

I had an unspoken goal to be the one person who’d been granted access inside prison walls with whom they felt comfortable enough to bare their souls, and I didn’t want my choice of clothing to be the thing that stood in the way.

I wanted to appear professional but not so professional that inmates would perceive me as unapproachable. I wanted to appear polished but not too “put together” in a way that prohibited participants from speaking honestly. I wanted to look attractive and likable but not so much that I would seem seductive.

I desperately wanted to avoid coming across as too professional for fear they wouldn’t feel comfortable opening up to me. I was terrified that they’d judge me as "unsafe," and I'd stand there, asking questions of an audience who would respond with silence and cold stares. I also wanted to appear calm, cool, and collected. Nothing must stand in the way of my goal.

They had to find me trustworthy, capable, attentive, responsive, and relatable if I wanted to gather meaningful data. And they’d probably form their impressions of me in the first few seconds based on how I dressed and the way I carried myself. Nobody talks about prison life with someone they feel is unapproachable.

So, I put together the perfect outfit and I walked into the Houston area prisons we were set to access. I wore baggy pants (sweat-wicking, because the air conditioning might not be working, and we were in Texas, in July!), and a loose fitting collared linen shirt with the sleeves rolled up so not to show too much skin or the outlines of my body.

And I’m terrified because, in this group of men, most of them were serving life sentences for horrific crimes.

Appearances matter.

Judging another person based on appearance seems to be part of human nature. We all do it to varying degrees, and I am no different. 

What I saw in that prison interview room was no less than 20 men at a time who wore white jumpsuits, menacing looks, and formidable statures. Needless to say, I was intimidated. 

I saw Black, Brown, and White men, most heavily tattooed, some small in stature, others as large as the actor Michael Clarke Duncan who portrayed 6 ft. 8 in. powerfully built John Coffey in The Green Mile.  

I asked several of them, “how are you doing today?” and one jovial looking, curly haired guy said, “I’m blessed and living victoriously!” I later found out he was convicted of the capital murder of four victims who he’d bound, gagged, and shot in the face execution style.

I met a tall, heavy-set, intimidating-looking man who, at the age of 17, was found guilty of shooting a homosexual young man who he and his friend had lured into their pickup on false pretenses (his story was highlighted in a 1995 Vanity Fair article). 

I met two other men, both polar opposites in appearance: one was a slight statured, shaved-head man tattooed with the word “Shutzstaffel,” German for “protective echelon” (the political soldiers of the Nazi Party), which ran the length of his shoulder to his wrist, indicating his affiliation with the White Supremacists. The other man was a very muscular, tall, Black man who called himself a “fighter,” who admitted that he initiated no less than 8 fights the first couple of days in prison.

I met a 30-year-old man serving time for manslaughter (aggravated assault with a deadly weapon) who talked about his face, neck, arm, and torso tattoos covering most of his body that boldly proclaimed his gang affiliation. He later told me the only way to get out of the gang was to have your tattoos cut off, which in his case and many others would mean he’d have no skin left. I’m not sure that qualifies as “getting out of the gang.”

I met an athletic young man convicted of child endangerment when the 3-year-old child entrusted to his care suffered significant damage to her brain such that she faces lifelong weakness on the right side of her body, she lost her peripheral vision, and she will never be able to drive a vehicle.

Alex Lickerman wrote about our tendency to judge a book by its cover:

“Our expectations of others are triggered by not only how they look but how they present themselves overall (what clothes they're wearing, whether they're clean-shaven, their accent, and so on). This wouldn't be a problem by itself, however, if it weren't also true that we're so often more influenced by our own biases than we are by actual evidence. When we have a powerfully positive or negative emotional reaction to someone upon first meeting them—often due to their overall presentation—it powerfully affects our reaction to the "content" we find inside, meaning their personality and character.”

I think it’s fair to say that I had initially judged the books by their cover and that my observations were accurate. However, once I got to the business of “reading the books,” or talking to these men, I understood that I had gotten it all wrong.

Stories of transformation.

My research challenged my preconceived notions about those who are incarcerated and about their potential for rehabilitation.

Recently, I read this personal account of transformation from someone I’m connected with on LinkedIn, Richard Mireles. He had a lot to say, and I would be remiss to omit anything from the quote. He said:

“I'm a formerly incarcerated person who was sentenced to 25 years to life & served 21 years in the California prison system. I took full & complete responsibility for all of my past decisions & the harm I caused, the ripple effects of my actions, was able to make amends to the person I harmed & was set free after my first board hearing. I never had a disciplinary write up in all of my term, stopped using alcohol & drugs over 22 years ago (never to use again), earned an AA degree with a 4.0, graduated cum laude with a Bachelor of Science degree & left prison 4 classes shy of an MBA. I earned a CADAC II with 6,000 hours as an AOD counselor on the inside, was certified as a Transformational Life Coach and trained over 60 three-day workshops, and I earned over 400 certificates of completion. I said all that to say this: I'm not a sub-human being that needs to be judged for the worst decision I made in my life nearly 25 years ago. I am a transformed man of God who made a series of new choices, transformed my thinking and beliefs about myself & others and now live to be of service to a multitude of communities as a natural expression of who I am!”

What I learned in my research was that Richard’s story is not the exception. One hundred percent of the men I interviewed had shown me they’d undergone remarkable transformation—a transformation that could only be explained by the power of God working in the hearts of men who, for all intents and purposes, had been “written off” by society. 

I witnessed a former White Supremacist, heavily tattooed with various signs of his former life, hug a muscular Black man, a self-proclaimed “fighter” serving a life sentence, saying “I love you.”  “I love you too, man,” the Black man said in return. 

I should also add that the “fighter,” in a separate conversation after my group interview, said that he’s never felt more freedom than he does right now. Here is a man imprisoned, serving at least one life sentence (maybe two; I didn’t get everyone’s full story of how they got there), saying he feels free. His freedom has been taken away by incarceration, yet he proclaims to be no longer bound by his crimes. The “fighter” has found freedom in the Christian life—in prison. Let that sink in. 

I met two men who’d earned their Bachelor’s degree in Biblical Studies while incarcerated, who now teach theological classes in prison and mentor a significant number of young men in their unit. One of them (Jason, serving a life sentence for aggravated robbery), co-authored the book, “Exiles: A Prisoner’s Daily Devotion,” and the other (Jesse, sentenced to life in prison for murder) is successfully parenting his son while imprisoned. I, along with others (including his wife) encouraged him to write a book about godly parenting from prison. I hope to read his book one day.

The men I met hugged one another, they prayed together, they wrestled together with difficult concepts that followers of Jesus have considered, like, “How do you know Jesus is real,” “If God is so loving, why does He allow suffering,” and, “Why does evil exist?” 

I saw the men I met lead worship in the prison church service we attended. They played important roles in church, from playing drums, to leading the choir, to writing and performing Christian rap songs, to organizing the church service, to preaching sermons. And outside of church, they lead Bible studies, they mentor other inmates, and they serve their fellow prisoners every way possible.

Many of the men I met want to start a ministry when they get out, and most are already engaged in ministry inside prison walls, spreading the hope and light they’ve found through participation in TUMI. 

What I learned from participants.

While I was so concerned with what to wear to prison, these men taught me that you shouldn’t judge a book by its cover. Judging the worth or value of someone by outward appearances (or by where they currently live, a.k.a. prison), or what the tattoos of their former life reveal, is just plain foolish. 

We all carry around with us conclusions we've drawn about other people through which we filter everything they say and do, often thinking they are worse than they actually are. But I would argue that forming a real opinion involves more cognitive work.

If we really want to understand our fellow human beings accurately, we must allow them to surprise us, to contradict what we think we know about them. We must go to scary places like prisons and allow our hearts to be changed by what we see.

I met people who are still serving time, but they are working toward a better future. These men are rewriting the book of their lives. Had I not looked past the “cover” of the book I saw when I first met them, I might have never heard the amazing stories of transformation. 

I learned that day that reading the book matters. It matters far more than just looking at the cover (the tattoos, the white jumpsuit, the menacing looks, the athletic build, the crimes they committed that landed them in prison years ago) while consciously neglecting to look inside. Outward appearance doesn’t reflect inner beauty.

It took a trip to prison for me to realize that what you’re wearing doesn’t matter.