Cycle Shorts

Zara blazer (similar)
Old Navy shorts
Dune London mules (similar)
Chanel handbag
Celine sunglasses
Celine necklace (similar)
Stella & Dot ring
Mango earrings
Location: The Exchange District – Winnipeg, Manitoba

I have a long and storied history with cycle shorts. Which is precisely when I never thought I’d wear them again.

I was a cycle shorts aficionado in elementary school. I’ve always known what I liked. And when I was ten, anything that made me look the part of the girl-training-for-the-Olympics that I wished I could be was what I liked. Cycle shorts topped the list. I owned what feels, in retrospect, like infinite number of pairs. In reality, it was probably about five. My two favourites were solid royal purple pair and a blue gingham pair printed with tiny daisies.

I chose the gingham print pair to wear for my first day of seventh grade. I was starting at a new school where I knew no one, in an Advanced Placement program I’d impulsively leapt at the chance to join months earlier but was feeling lukewarm about by that point. The idea that my outfit might contribute to my new classmates’ first impression of me never crossed my mind. That is, until I walked into homeroom in my blue cycle shorts, which I’d paired with an oversized blue Teddy Bears Picnic t-shirt and white sneakers. I knew instantly that I’d made a grave error in sartorial judgement.

The error wasn’t the one you’re expecting. My blue cycle shorts didn’t mark me out as uncool or immature. I was unprecedently popular in seventh grade – more popular than I ever had been in school, or ever would be again. My outfit made me look just as weird and nerdy as all of my Advanced Placement classmates. They immediately recognised me as one of them… and while I would never argue that I’m not a bit eccentric (because I definitely am), I was not nearly weird enough to fit in with that group. I came to school with no imaginary friends. I’d never played Dungeons and Dragons. Never read Lord of the Rings, never played a video game that wasn’t the original Super Mario Brothers, never even touched a Magic card. If you’d asked me about Pokemon, I probably would have responded, “Bless you.”

I was not one of them. And no amount of birthday party invitations could convince me that I wanted to be. My seventh classmates were nice enough people, generally, but we had nothing in common beyond above average test scores. That homeroom is the only place where I’ve ever stood out for being too normal. Strange situations lead us to behave in strange ways, and I leaned into normalcy that year like I never had before (and never would again.) I gave up my cycle shorts within days, swapping them for overalls and, before the school year ended, denim cut offs. To this day, denim shorts remain my shorts of choice.

But… cycle shorts came back last season and I found myself eyeing them with a level of interest. Only in black, of course. They could look quite sophisticated, I thought, if I paired them with something more elegant than a Teddy Bears Picnic t-shirt. Still, I hesitated.

When we were in quarantine, I ordered a lot of loungewear from Old Navy. Mostly leggings. I didn’t actually own leggings, before quarantine, but if ever there was a time for them, that was it. So I bought a couple of different styles to see what I liked. (The answer, it turns out, is that I don’t like any of them very much – I will always be a sweatpants girl.) I threw a pair of cycle shorts into one of those orders, because spending an extra twenty dollars meant, improbably, that I would save an extra twenty-five, effectively getting them for free.

I’ve worn them once or twice this summer, usually with my oversized linen shirt and my beloved Birkenstocks for a trip to the grocery store. But as summer began to reach its inevitable end, I considered that by next year, cycle shorts may be one of those trends that we look back on with a laugh. This might be my one chance to redeem myself from my past cycle shorts choices. So I took it.

And I admit, I felt pretty good about the result. In fact, I’m not sure cycle shorts have any right to look this sophisticated. This is exactly how fabulous my seventh grade self thought she looked when she left for her first day of school. But everything is a matter of perspective. I wound up hating that seventh grade outfit, wishing for something like this instead. And yet, I’m sure if I’d showed up at school dressed like this, I would have been laughed right out of homeroom.

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