Middle school is easily the worst phase of anyone’s life. You will never look worse. You will never be dumber. You will never have fewer friends. Life in middle school is dreadful. I don’t know one person who doesn’t look back and think, You couldn’t pay me enough to go back and relive it!
Well, we’re not going to show you middle school pictures. I refused. So, we’re going to show you the next best thing: 5th grade. This hurts a little, so try not to judge too harshly. Or do, because that’s the whole point. Bringing us to our knees in sheer humiliation. That’s what we live for. We’re masochists.
At this point, I still had a gross gap between my teeth, so I went through life smiling like this – mouth shut, fierce defiance. And let’s be clear: I thought I was so cool. I was the best thing ever to happen to anyone around me. It was my most naive phase. Jessi has always been super hot, and I think this picture speaks to that. Pure confidence! My whole life would’ve been better had I felt even one-tenth of the confidence she’s always known. But still, a crocheted vest with jean shorts? Maybe a little less confidence here wouldn’t have been inappropriate… LOVE YA, JESS JESS!
As always, click to enlarge for gory details. Just vote and put us out of our misery.
[And if you've never played along before, check here to see all of the awesome moments of our history. We'll be bringing you Who Wore it Worst each week through the end of the year, so stay tuned!]







I’m disapointed there isn’t any arm-shelf action.
I’m also going to find some pictures of myself and send them to you so I can participate in a WWIW one of these days. Some of my photos will probably blow you out of the water… seriously. I was/am/always will be the most awkward child/person ever…
It has actually been fun finding all the horrors of Lifetouch school photography and laughing at ourselves! Please, please, please find some of you!
First off, I would like to note that I have asked repeatedly for us to put up some pictures from present-day because we look so amazing but Jena refuses and insists on putting up the worst photos ever made of me.
Second, Jena, I believe you are wearing lipstick in that photo. Oh, how some things never change!
Third, I adored that sweater vest and my army green shirt. I thought it made me look like a girl from 90210. I bought that entire outfit from JCPenney and it was Arizona brand. Adored Arizona in the 5th grade.
Fourth, how pitiful were we? Confident, yes. I thought I was da bomb but in actuality and at a mature 25 I recognize the hotmess that I was.