I Tried—and Failed—to Wear This Season’s Biggest Trend, but Learned a Lot in the Process

I very distinctly remember the first time I saw Kim Kardashian West wearing bike shorts. It was summer 2016 and my immediate reaction was “What is she thinking?” Even though she’s known for wearing enviable fashion-forward outfits on a near daily basis, I thought the spandex number looked silly and unfinished—basically, solid proof that it was impossible to turn this style into something chic. Turns out, I was a fool.

Here we are, three years later, and you know which trend is still going strong? Bike shorts. They’ve since appeared on the runways at Chanel, Fendi, Stella McCartney and Saint Laurent, among others. Almost every supermodel and fashion editor has been photographed wearing them at various fashion weeks. They’ve even popped up on the red carpet (though, to be fair, Demi Moore did it first).

As part of an ongoing sartorial experiment, I’ve been challenging myself to reconsider a trend I find to be confusing and weirdly intimidating. By that, I mean I’m forcing myself to wear said style for a few days, in the hopes that I might finally discover what all the fuss is about. However, after just three days I was forced to admit that even I, someone who gets paid to write about fashion on a daily basis, just cannot get on board with bike shorts.

I eased myself in on day one with a pair of bike shorts from Athleta that are actually meant for working out. I casually paired them with a loose long-sleeve tee from The North Face and some funky sneakers from New Balance. Sure, I looked like I was probably headed to the gym, but isn’t that what athleisure is really all about? Besides feeling a bit underdressed, even for a lazy Saturday, the only aspect of the look that bothered me was that the shorts tended to ride up when I walked for long stretches. Even so, the first day of the experiment wasn’t too bad.

Then came day two. It was time to really push myself, which meant trying to turn sporty spandex shorts, a super-femme blouse and kitten-heel mules into a cohesive outfit, as I’d seen so many fashion bloggers do before. But no matter how hard I tried to make it work, I just couldn’t find a common thread that could pull those items together. I honestly felt like these separates were actually fighting one another with an aggression reminiscent of the bloody brawl between feuding news teams in Anchorman.

I’d tried on and rejected every trendy headband, fun pair of statement earrings and chic handbag in my arsenal to try and make it work. It didn’t matter how cute my new favorite mini handbag was; I still looked like a woman who had spent so much effort getting into a pair of Spanx that it caused her to completely forget her skirt. In the name of science fashion, I forced myself out of the house anyway.

If ever you find yourself feeling uncomfortable in your outfit choice, not because it doesn’t fit but because you’re not entirely sure that it works, I have discovered the ultimate solution. Attend a boozy brunch with women who you know and like, but who are definitely not close enough with you to be brutally honest. After a few mimosas they will assure you that you look adorable. Just like Kendall Jenner. For a while, you’ll feel great. And then you’ll leave to go home and the desire for pants long enough to at least cover your upper knee will resurface more abruptly than Kahlessi’s turn from admirable queen to murderous psychopath.

On day three I decided to revisit the inherent sporty nature of bike shorts and opted for a high-waisted pair, along with a full-coverage sports bra, classic white sneakers and a jean jacket. It’s a look that’s sexier and edgier than I typically go for. As a result? I never ended up leaving my apartment.

I scoured Pinterest, Instagram and our very own collection of fashion articles, hoping to discover an outfit that I thought might work for both my sense of style and my body type. I pinned, liked and even got butterflies looking at women who had figured out how to make bike shorts actually look good. But when I went to translate it on my own, nothing would click.

It felt embarrassing. I’d failed. Miserably. But as the old saying goes, what doesn’t kill you makes you stronger, and I’d be damned if I let bike shorts be the death of me.

As a fashion editor, I feel like I should have some level of expertise when it comes to taking the top trends of the season and transforming them into something any woman can wear with confidence. What I learned from this failed experiment is that not every trend will work for every woman—even if that woman is myself. As for bike shorts, I just felt naked or like I’d forgotten to put on pants and was walking around in my (albeit very full-coverage) underwear. The shorts themselves just didn’t feel like me, despite deploying all my best styling tricks. But that’s OK.

It’s sometimes necessary (and completely acceptable) to remind yourself that it’s fine to pass on a trend, even if you admire the way it looks on others. On the flip side, it’s also totally OK to test-drive a look that you’re curious about and bomb spectacularly. Then, when you come across a photo of yourself in whatever horrible outfit you just couldn’t pull together however long from now, you’ll be able to say, “What was I thinking?” and laugh like a fool. (Unless, like I did, you delete any and all evidence that you ever wore bike shorts in the first place.)