For four years, this year’s Middleton High School seniors said they looked forward to the end-of-school year tradition of taking a week to dress up in themes — including in clothes typically worn by the opposite gender.

But school officials last week asked students not to participate in cross-dressing day to avoid offending or hurting students at the school who are transgender, or questioning their gender identity.

“It may seem like harmless fun, but if it belittles any other group of students, no matter how small the population seems to be, that’s just not what we want,” said Middleton-Cross Plains Area School District spokesman Perry Hibner. He said the school sought to show students that even actions with good intentions can be insensitive

Senior Randy Perez, 18, was one of the 20 students who came to school on June 4 dressed up anyway — wearing a pink dress and headband with flowers attached. He said the administration’s decision reinforced gender stereotypes.

“You’re identifying what people can wear based on gender norms and preconceived notions of what you’re supposed to wear and I found that hypocritical if you’re trying to support the (transgender) community,” he said. “That defines roles even more than they already are. We are trying to break them. If I had worn a dress to school any other day, it wouldn’t have been an issue.”

Perez said he was sent home Wednesday for one day and faced not attending graduation for cursing at the principal after being told to change his clothes. Perez apologized and will now participate in graduation.

He said no one intended to offend or mock any other students.

Katlyn Tolly, a senior, said she didn’t think anyone had any intention to harm or offend any one, but “there will always be certain students who take it too far, which will offend people. So the situation should be avoided all together.”

The cross-dressing theme came after a day students dressed like the elderly, which also caused a stir when students arrived with wheelchairs and walkers. School officials said the students acted in a way that “mocked the elderly and people with disabilities,” according to an email sent June 2 from school administrators to students and parents.

Sean Benedict, a junior and a member of the Student Voice Club, said his group approached the School Board in May to discuss issues related to gender and race, which likely prompted administrators to take a look at the cross-dressing day tradition.

“We really wanted to stress the importance of sensitivity and safety for underrepresented students,” Benedict said. He said he believes cross-dressing day is offensive.

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In explaining their decision last week, district administrators said at one time it was acceptable to wear blackface and now it is unacceptable and offensive. Perez said the comparison upset him and other students.

“To equate (an) action that was taken purposefully to be malicious and hurtful to us dressing up in our senior week as we’ve done in the past … to equate his own students to the kind of people who would participate in that was really upsetting to a lot of us,” Perez said.

Senior Vaughn Kottler said the analogy “is far too strong and far too unrelated to what’s going on.”

“I think that what they are trying to do is make those who struggle with gender and sexuality feel comfortable and have freedom to dress as they please, but the way they are doing it is controlling the dress code of others and this is not a great way to go about achieving that,” Kottler said.

Hibner said administrators didn’t mean to equate the students with bad people, but sought to show that those who wore blackface probably didn’t think they were being offensive at the time.

Tim Michael, GSA outreach manager for the Gay Straight Alliance for Safe Schools in Madison, said Tuesday he receives calls from schools every year with questions about cross-dressing themed days.

He said harm can come from an event such as a cross-dressing day because transgender students struggle daily with having their gender identity recognized by others by using the right name or right pronouns, or by wanting to wear clothes they feel most comfortable in and sometimes can’t.

A day like this often plays out with straight boys wearing dresses often in an oversexualized manner, he said, which also brings up issues of misogyny.

“There’s a history in our country of men in dresses being funny — people think it’s funny,” he said. “I’m sure the majority of people have probably never had anyone sit down with them and talk about why we need to rethink this, and why this isn’t as funny.”

Michael said there were some students in the GSA at Middleton High School that supported the cross-dressing day because it gave students a chance to explore gender. But had the entire grade participated in the cross-dressing day, some GSA members may have felt differently, he said.

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