By: Akiva Bryant
Out of uniform… or are we? In a school where uniforms are the day to day requirement, free dress days feel like a breath of fresh air for students. A chance for them to show the school who they really are. Lately, however, not everyone feels this way. There have been conversations amongst students and faculty about the current out of uniform policies.
One controversy involving free dress days is the fact that for some of them, you aren’t able to dress out unless you pay a fee of $20. Although the $20 is usually contributed to a charity such as the Horizons program, it still causes frustration among students who want to participate in these days as much as possible. Senior Sophie Hylton ’24, a thespian and ultimate frisbee player, best explains this frustration.
“I wish that we had more out-of-uniform days, where anyone could be out of uniform without having to fulfill some sort of requirement,” Sophie said. “I understand that they’re going to a good cause, but paying $20 once a month is just too much. We should have some more out of uniform days that are just for fun.”
Sophie believes that out of uniform days are beloved by students.
“They’re seen as a reward or a way to demonstrate that you’ve done something good like donating to a cause or something to rile up school spirit before a big game.”
However, she feels that an aspect of the rules are unfair.
“I think it’s ironic that we have a dress code on out of uniform days, where they’re concerned about how much skin we’re showing,” Sophie said. “And you look at what the cheerleaders wear and they show so much skin. It’s hypocritical.”
Out of uniform days often come with students getting dress coded for the clothes they wear. This is seen as unfair to those who don’t think so badly of what they wore. However, Lillian Stokes ‘26, a softball player and wrestler, believes that certain things should not be worn.
“For free dress days, we should follow the rules of not showing the stomach, the breast and the butt,” Lillian ’26 said. “Since we’re a conservative kind of private school, I feel like we should probably follow that.They have tours walking around and they want Woodward to seem like they really adhere to the dress code.”
A lot of disagreements stemmed from the Neon Dress Spirit Day on August 18th. Specifically, a policy called “neck-to-knees” or “shoulder-to-thigh” was greatly enforced. Students who violated this rule, which states that an outfit must be covered from shoulders to legs with no gaps showing their skin in between, were dress coded.

Dean Underwood, the Associate Dean of Students, wants to make one thing clear. Neither he nor Dean Thomas create the free dress policy. They only enforce it. However, he has much to say about it.
“While our out of uniform days are a relaxation from our normal uniform, we are still here to do business,” Dean Underwood said. “We’re still here to learn. We’re still here to work. We’re still here to be professional and to teach professional. We have people coming on campus for various things. It needs to look like a school, not a party.”
He relates out of uniform days to free dress days that may happen to students when they get full time jobs.
“In a workforce when they have a dress down Friday, they don’t show up like they’re going to the beach,” Dean Underwood said. “They don’t show up like they’re going to the club. They show up like they’re ready to work in a polo or something like that.”
All in all, Dean Underwood states that he just wants to help students be their greatest.
“[Out of uniform days] should be special,” Dean Underwood said. “It should not just be a free for all, so treat it like it’s special. Walk in and look your best.”