Federal District Court Judge Richard Gergel wasn’t whistling Dixie when he said that the alleged Charleston church shooter, Dylann Roof, had a high IQ. Representing himself, the 22-year-old defendant to 33 federal charges including murder, may have already introduced a potentially winning appellate issue — “reversible error” — into the trial record, before the presentation of evidence has even begun.

Roof has been wearing his prison uniform in front of a jury, something that courts have said can be unduly prejudicial and award a retrial to someone who’s convicted in a prison jumpsuit.

I had entered prison (for identity theft) after I was tried as a free person, free to wear whatever I wanted. I was also tried once while I was incarcerated. For another trial in February 2009, my mother brought to court the wrong pants — her pants and not mine — and they fell to my ankles because of their size and the fact that no belts are allowed in lockup. I had to sit in front of a jury in a vintage sweater from the posh Manhattan boutique Henri Bendel above state-issued, elastic waist jeans with hems cut by nail clippers. I assume that the jurors knew I was incarcerated because my get-up was so bizarre. They couldn’t come to a consensus and my trial ended with a hung jury. The charges were later dropped.

I often wondered how I could appeal if I had been convicted since I was wearing half civilian clothing and half prison uniform.

Trial fashion seems of little consequence but a large body of American jurisprudence is devoted to it and people have seen their criminal convictions be reversed based on what they wore to court when their guilt or innocence was determined. In 1975, the Supreme Court decided in Estelle v. Williams that the government may not compel a criminal defendant to wear prison attire at his or her trial, at least where he or she is not being tried for a crime committed in jail. Every accused person has the right to appear before a jury in plainclothes.

Compelling the accused to stand trial in a jail uniform usually works against only those who cannot post bail prior to trial, triggering equal protection concerns. Just last week, the City Council of New York City voted to ban jail uniforms in courtrooms. Because so many defendants who are held pretrial are poor, allowing them to appear in outfits that make them appear guilty — as opposed to those who can afford bail and appear in regular attire — violates their rights. In criminal courts, clothes can make the man.

Of course, a defendant can waive his right to appear in street clothing. It’s not unheard of. A defendant in Washington state wanted to wear his jail uniform but was denied that choice. Terry Caver explained that his jail clothes “represent that I’m in here, that I’m not on the street. It represent[s] what’s really going on in my life. I don’t want these people thinking that I’m on the streets when I’m not on the streets.”

The trial court said “it causes much mischief if the defendant is clothed in regular jail garb” and denied Caver’s request. But make no mistake: the ‘mischief’ described by the court had little to do with courtroom shenanigans and everything to do with the fact that appellate courts have overturned convictions of people who wear their prison clothes to trial.

It’s unclear if Roof specifically waived his right to a regular outfit. He’s tried to waive his right to a jury trial and relinquished his right to counsel. He likely wouldn’t think twice about the right to be tried in civilian clothes.

And, regardless of what he wears, many of the jurors have heard of Roof’s case and been exposed to some press coverage about it. It may be hard to see how seeing him in a jumpsuit would affect a juror’s view of him when he’s already received so much attention. But, between the first and second juror panels in September, Roof changed from his jumpsuit to grey pants and a blue sweater when he was represented by counsel. Then he wore prison stripes as he represented himself. Now that he’s jumped back toward the protection of the Sixth Amendment and agreed to be represented by counsel again, if he changes his clothes and the judge never specifically inquired about his waiver of his right to plainclothes while he was self-represented, any conviction might be in danger since he spent some time representing himself looking like a con. It would be a case of first impression — meaning the fact and the law haven’t collided in this way before.

But what has been usual about United States v. Roof? Shakespeare once said that the soul of a man is in his clothes, almost like he knew about this case. A higher court might wipe out any conviction and death penalty against Dylann Roof based on what he’s been wearing.

And if they do, then we will start all of this again.

Chandra Bozelko is the author of Up the River: An Anthology and writes the award-winning blog Prison Diaries. You can follow her on Twitter at @aprisondiary.