Teachers' Most Embarrassing Wardrobe Mishaps At School

When I began working as a high school teacher, I realized that although it’s a profession that is to be revered, it can also come with some absolutely “Funniest Home Video”-worthy style moments. 

Take the time I was running late to work. I opted to do a simple makeup job that’d normally include filling in my eyebrows. I skipped that step, threw on lipstick and headed out to shape brilliant minds. One of my 11th graders approached me with heaviness and concern in his eyes, asking if I was OK. I responded with an affirmative, “Yes, why do you think I’m not OK?” and he said, “But where did your eyebrows go?” Imagine the horror I obviously couldn’t fully display, due to having no visible eyebrows with which to express myself.

I’m certainly not the only teacher who’s had a wardrobe malfunction or a makeup mishap in the classroom. Below are tales from teachers around the world who’ve shared some of their funniest, most awkward stories with us, via Facebook and interviews. (Some preferred not to share their full names to protect their privacy.)

Feeling Breezy

“I was walking my students up to class from breakfast and my entire class was behind me snickering. One of the girls said, ‘Hey, Ms. Williams, you got a big ole hole in yo pants.’” I put my hand back there and my whole ass was hanging out and nobody said a word. I had my principal take my class, went home to change, and came back to give the class a lecture about not letting me look crazy out here because I’m a reflection of them.” ― Ribbon Williams

Super Bowl Vibes

“I was still actively breastfeeding and during a class one of my boobs became so overly filled that it popped completely out my bra. I absolutely had no idea that I was giving everyone Janet Super Bowl vibes. Thankfully the kids hadn’t noticed. Or at least I hope they didn’t.” ― LuLu

Wigging Out

“I was dancing and singing for a demo class in front of prospective students and parents. Overly excited, I never felt my wig sliding off my head. I then look over to my Chinese teacher as she whispers to me, ‘Shantese, your hair!’ I replied, ‘What’s wrong?’ She points and says, ‘It’s on the ground.’ My face was completely red. I danced my way over to the wig, picked it up, ran out, went to the bathroom to fix it, and came back in and completed my demos. That day I actually signed up all of the kids in that demo class.” ― Shantese Clark

Transparency Isn’t Always The Best Policy

“A few months ago, I ordered a dress from this popular Chinese site. I wore the dress to school and thankfully I was wearing a jean jacket to accompany it. I also wondered why some students were walking past me, looking shocked but not saying anything ― which is customary as a foreigner in China, so I paid it no mind. Well, the dress was actually very see-through, to the point that you could see straight to my underwear. I quickly covered it up with my jacket.” ― Natavia Turner

These Boots Weren’t Meant For Walking

“Two girls start fighting at the top of the hallway and of course, I would be the only teacher who would even attempt to break it up, so I took off full speed in cowboy boots ... TOTALLY forgetting I, 1. did not have on sneakers and 2. am EXTREMELY pigeon-toed. I turned and took exactly three strides before I clipped my own foot, SPLAT and slid on my face down the hall in the middle of 150 students. To make it worse, I slipped twice trying to get up, and ripped the knee of my pants. The kids were mortified and the teachers were frozen. I got up and hobbled toward the fight and successfully broke it up. I ended up bruised and the butt of jokes for weeks!” ― Monique Taylor-Gibbs

Heel-arious

“I always had a slight fear that this would happen, but not in the way that it did. My principal finally gave me the green light to show new potential parents and their children our facilities. As I led them out into the courtyard (which was still under construction), a parent made a suggestion that maybe we shouldn’t go too far into the rubble. However, trying to be a star, I decided to grace the rubble’s presence with my stiletto shoes and as I turned to walk back toward them, I had come back with one missing heel. I had to finish the tour walking high, low, high, low because I didn’t bring any other shoes for the day.” ― Sabrina J.

Skirting The Issue

“Rushing to use the bathroom during parent-teacher conference night, I thought not too many parents would arrive because my class had been doing well for the quarter. I tucked my shirt into my skirt before exiting the bathroom and heading up the hall, I could hear in the distance a few ‘Oh mys’ and one ‘Is she drunk?’ before another teacher shuffled me into their classroom, letting me know that my skirt had been tucked into my stockings. Let’s just say I called in sick the [next] day.” ― Brittney F.