September, in all its gourd-scented delicacy, is a time for reinvention. Just as the leaves undergo a total makeover, turning from green to brown faster than Price Chopper avocados, we feeble humans find our physical appearance ripe for change along with the seasons. As we bid farewell to the sweaty handshake that is the month of August, it’s time to turn our attention to September and all the sartorial opportunities that it brings.

A self-proclaimed fashion maverick, I spent the first ten years of my education shrouded in uniform. Dressing myself was a foreign experience, even a cause for panic. There were days, of course, where we could dress in our own clothes in the name of charity – it was a cause for celebration, much planning and perhaps even a trip to Abercrombie & Fitch. I picked out my outfit the night before, prepared to “wow” my peers with my grasp on personal style at such a young age. I pictured myself strutting across the playground, Fergie’s “Glamorous” playing in the background, to the whisperings of students and teachers alike: Who’s that chick? Did she get lost on the way to New York Fashion Week? How does she pull off wearing a single blue feather earring in such a way that makes her look cool and quirky and definitely not the descendant of pigeons? 

Instead, someone literally asked me: “Were you in a rush when you picked out your outfit this morning?” Like the calm, collected human girl I am, I played it off and replied something like “Oh, yeah, I was running so late! Just picked out the first thing I could find! Let’s all just go listen to NOW! That’s What I Call Music! and forget about my bizarre OOTD.” It was 2008, and the fact that I wasn’t wearing a full Juicy Couture sweatsuit meant I had invariably failed at life.

Because hindsight is 20/20, I can confidently say the ensemble I so carefully picked out was truly horrendous and someone should’ve stopped me. As was true for most of my middle school years, it looked like I got lost on the way to a Blink-182 concert on my way from clown college. I sported mustard yellow tights under a light wash, cut-off denim miniskirt accessorized with turquoise converse. The real pièce de résistance was a purple graphic tee that read, in orange lettering, “SAVE THE DRAMA FOR YOUR MAMA.” It’s still in my closet today, just in case it comes back into vogue – which might be difficult, since it could hardly be considered fashionable in the first place.

Since that fateful day, I’ve significantly retreated from my gut instinct and tried to dress more like someone who could potentially be featured in a street style blog if the photographer was in a time crunch. While I formerly dressed to stand out, now I dress to fit in. Seventy-five percent of my shirts are striped, and I deal with a palette of blues, greys and whites so I can blend in with the sky no matter the weather. As my graphic tee collection dwindles into nothing, I can work on making less literal statements with my outfits going forward. That fateful day of eigth grade, I declared my personal identity in terms of style, unafraid of the consequences. And while my outfit was the absolute worst, the moxie with which I wore it has never gone out of style.