In his dissent, Justice Hugo Black disagreed with the Court’s finding that the school district did not have a legitimate justification for the restriction of the students’ “symbolic speech” by prohibiting them from wearing armbands. He wrote, “While the absence of obscene remarks or boisterous and loud disorder perhaps justifies the Court's statement that the few armband students did not actually ‘disrupt’ the classwork, I think the record overwhelmingly shows that the armbands did exactly what the elected school officials and principals foresaw they would, that is, took the students' minds off their classwork and diverted them to thoughts about the highly emotional subject of the Vietnam war.”

Black also disagreed with the Court’s expansive view of student rights and stated that “if the time has come when pupils of state-supported schools, kindergartens, grammar schools, or high schools, can defy and flout orders of school officials to keep their minds on their own schoolwork, it is the beginning of a new revolutionary era of permissiveness in this country fostered by the judiciary.” While reaffirming his belief in the freedom of speech, Black noted that he this does not mean that any person “has a right to give speeches or engage in demonstrations where he pleases and when he pleases.”

Furthermore, Black explained that school officials are permitted to place limitations on the speech of teachers and students, writing that “[t]he truth is that a teacher of kindergarten, grammar school, or high school pupils no more carries into a school with him a complete right to freedom of speech and expression than an anti-Catholic or anti-Semite carries with him a complete freedom of speech and religion into a Catholic church or Jewish synagogue.” He noted that schools “are operated to give students an opportunity to learn, not to talk politics by actual speech, or by ‘symbolic’ speech.”

Black warned that the Court’s decision would have dangerous ramifications on the authority of school officials and the values of the public school system. He wrote, “[u]ncontrolled and uncontrollable liberty is an enemy to domestic peace. We cannot close our eyes to the fact that some of the country's greatest problems are crimes committed by the youth, too many of school age. School discipline, like parental discipline, is an integral and important part of training our children to be good citizens-to be better citizens. . . One does not need to be a prophet or the son of a prophet to know that after the Court's holding today some students in Iowa schools and indeed in all schools will be ready, able, and willing to defy their teachers on practically all orders.”