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Teacher drag: a reflective update


When I first was getting ready to move out of my childhood home and into a condo with V, my mom wasn’t (outwardly) upset about her oldest daughter moving out. Instead, she was very upset that she wouldn’t get to see my “teacher drag” every morning as we both got ready for work.

(The idea of “teacher drag” stems from a poem I wrote when I first started teaching. A year prior,  I was doing teaching observations and simultaneously being a Resident Assistant, one of my residents saw me early one morning. She remarked, “You look very… Republican. Like a young Barbara Bush.” I couldn’t help but laugh, but her comment stuck with me. This incident inspired the phrase “teacher drag.”)

When I saw how upset my mom was, in my immediate need to comfort her, I swore I would send her a selfie every morning. Then, she told me to instagram it, as she was trying to get more familiar with instagram. I started using the hashtag #TeacherDrag, which I had only used once or twice before, the week I moved out, and what started as a sweet inside joke between me and my mom grew into something much larger. My friends started texting me how they loved seeing my outfits, and when I changed the privacy settings on my instagram and made it public, I suddenly had a slew of fashionistas (and teachers) liking my posts and following me.

One of the first #TeacherDrag outfits

I have to admit, before #TeacherDrag was a thing, there were some mornings I just didn’t care. I never quite looked like I’d just rolled out of bed, but there were days where maybe I didn’t wear the most flattering outfits, or my hair was a mess, but it didn’t matter because I was spending the day with teenagers.

#teacherdrag #ootd #nyandcompany #favoritedress #howifellinlovewithevamendes

A post shared by Kailynn (@thegingersass) on

Somehow, #TeacherDrag turned me into more of a fashionista. I’ve always loved accessories, and I’ve been known to base entire outfits around a necklace, but this hashtag has definitely made me put my forgotten accessories to work! I’ve received texts when I haven’t posted my morning photo before 7 (lol), and I feel a sense of importance with what I’m doing. When I was in that elevator that morning a few years ago, I thought #TeacherDrag had to be pearls and power suits. Pearls still are a staple of my wardrobe, but I’ve ditched the power suits to be more fun. Now, I realize what I wear to teach can be young, fun, and exciting without breaking any dress codes.

So, my fellow teachers, I ask you this: What does your #TeacherDrag look like? Share it on instagram using the hashtag and let me know!

Oh, and don’t worry– it may be Summer Vacation, but I’m teaching Summer School the entire month of July. #TeacherDrag #SummerEdition is a thing. 😉


It seems as though karma is kicking me in the butt today, as today’s prompt is to write a narrative poem… which is one of the first assignments I assigned my students this year, much to their dismay.

I’m cheating a bit with this poem and posting a piece I’ve been working on. I performed it a few weeks ago, and it was met pretty positively… who knows? Maybe my first book will be on my experiences as a drag queen.

My drag show go-go juice, nice and fresh at 5:55am every morning.

My drag show go-go juice, nice and fresh at 5:55am every morning.

(tentatively titled “Drag”) 

I have a new job.

I am a drag queen.

It’s a pretty sweet deal.
every day I wake up at 4:15 AM,
and I spent about an hour
doing my hair, my make up, and drinking my coffee.
I leave the house by 5:30,
and I arrive at my stage around six.
I either spend an hour making my soundtrack for the day,
or getting my props ready.

At 7:20 it’s show time.
I greet my audience,
and I wait for them to shut up
so I can begin.
I call bitches out on it
when they have their cell phones going off during my performance,
and I’m sure to call out the person 
who looks like they’d rather be getting a root canal.

I repeat my act 3 to 5 times a day,
with only a few breaks.
After my day ends,
I pack my bags,
take off my heels,
and head home,
for I just spent the past 12 hours on stage.

I finally arrive home,
and I don’t know who I am anymore.
I look into my closet,
and I wonder whose house I’m in.
Teacher drag has taken over my life–
I have blazers.
Sweater sets.
Sensible shoes.

I dress in teacher drag,
and there’s nothing I can do about it.
I am a drag queen.