I found myself strolling through the “back-to-school” section of Walgreens the other day, wistfully thinking about how satisfying a fresh notebook is, and how nothing in life is better than brand spanking new office supplies (do I have issues?). Which made good ol’ back-to-school memories flood my brain. 

I spent a painful amount of time on my back-to-school outfits starting in middle school. Before that I think my mom just put me in a vest and a turtle neck on the first day … and on picture day. A vest. (Why, woman, why!?) But after that, painful amounts of time were spent trying to look like Britney Spears on the first day of school. Sigh. The early 2000’s … am I right? 

I really don’t know what the balls I thought was going to happen if I wore the “end all, be all outfit” to school on the first day. I clearly watched waaaay too many teen movies and was expecting all of the cute boys and popular girls to be all, “wow … who’s that girl? Oh wait! It’s Kate! No way! But she’s so cool now! Let’s be friends forever!” That never happened. Instead I sit here years later thoroughly mortified for making my mother buy me such expensive jeans to impress such clowns.  

I’m sure we all have our favorite back-to-school outfits and memories, but I thought I would share a few of my faves with you in hopes you will share with me yours so I feel less shitty about myself. 

1. Tweezing my brows: Yep. That happened a few days before 8th grade started. I had bushy ass eyebrows that were so bad, people, including my hair dresser at the time, wanted to tackle me to the ground and wax them. But no, I wouldn’t let them, for I didn’t want to grow up. That’s until I started thinking my life was a teen movie, and thought my crush would only like me if my eyebrows were perfect. 

After I removed 95% of them, yes … 95% … making them skinny and uneven, my mother asked me what had I done? I said nothing. Nothing was different. My eyebrows did not get smaller. And I walked away … mortified that I had destroyed my face. And wanting her to hold me. 

2. Wear a bra, Kate: I mean I knew life sucked in a strapless bra even before I wore one. Because my mother walked into my room the day 7th grade started and insisted I wore a sports bra to school. I was mortified. I literally just wanted to cry. And for the rest of that first week of school … and probably the next month or so, I would go into her room in the morning and ask her if I had to wear a bra, praying she would say, “no, Kate … your taas aren’t growing at all. I was just kidding. Free ball for the rest of your life.” Yep. I was a freak.

3. How low can you go: Fast forward to high school, when Britney Spears made it super cool for your jeans to rest right above where your vagina started. AKA sitting and bending down was impossible. I, again, made my mom buy me these amazingly expensive jeans from Lucky that had faded pockets on the ass and said “lucky you” when you pulled down the zipper. Looking back … it was a little whorey. But that is neither here nor there. I wore them on the first day, and when I sat down in my homeroom, realized my entire ass crack was out. Not just the tip of the crack. I mean FULL. CRACK. Say crack again. CRACK.

I remember slouching so badly in my seat that I mine as well have been horizontal. I seriously still have lower back problems because of those damn jeans. Did I stop wearing them after that? Uhh … did I mention Britney Spears deemed uber low risers super cool? With that being said, all of my high school saw my ass crack every day from 2001-2005. You’re welcome, world. 

So there are my embarrassing tid-bits for the day. Now whatchu got?