It's a question that has plagued men for generations.

Are My Pants Too Short? A Title Investigation

If I weren’t so judgmental of others, I probably wouldn’t be worried about the pants I’m wearing today. But, owing to a certain lack of confidence when it comes to style, I silently try to build myself up by noting the sartorial mistakes of my fellow commuters, shoppers, diners, and humans. I’m hardest on myself, of course. When someone walks past me with both buttons of his blazer securely buttoned,1 I can tell myself that they don’t know any better, and as such should be held to a different standard.

And, like a lot of self-doubt, my feelings about my pants are probably inaccurate. My coworkers have assured me that there is nothing wrong with the pants I’m wearing. But, I hesitate to believe them. My mom also said I could be a champion tee-ball player, but the scouts never showed up. The point is, people lie to you and consider it mercy. When it comes to your clothes, you can’t trust anyone but yourself.

Which is why I’ve opened this investigation. So much menswear coverage is either situation-based or purely aspirational. Sure, we’ll tell you which awesome shoes to wear, the dope jacket to add to your rotation, and how to kill it at a wedding or bar mitzvah.2 But we rarely take on the day-to-day challenges of dressing well and feeling comfortable. Put another way, mostly we talk about style in the future tense. This is happening right now. I’m wearing these pants right now. There is no more pressing fashion issue than what you’re wearing right at the moment you’re wearing it.

The Case: My Pants

They are khakis, purchased recently from a certain Japanese fast fashion brand that will remain nameless because they haven’t yet advertised with Title.3 In a style move that will surprise no one, I have paired these light khakis with a navy V-neck sweater over a red checked shirt. I am dressed as if I were cast as a dad in a car commercial—but, like, a really nice car: relatable, non-threatening, current but not so modern that you wouldn’t be able to reuse the footage in another ad campaign next year.

I would feel perfectly confident in this outfit. In fact, I wear something similar almost every day, sometimes with a blazer. But these pants. They are long enough to softly brush the top of my shoes, but not long enough that they aren’t constantly caught behind the tongue of my Nikes, which makes the pants suddenly seem like joggers, only with somehow less shape.

Compounding the problem of length is their fit. Somehow I have entered a period in my life where I am gaining weight even though I haven’t changed my lifestyle at all. I still work out regularly, and—as per most dietician’s recommendations—I consume the bulk of my calories after 10pm. But so anyway, I’m finding that pants represent this impossible balance between waist/butt comfort and calf-compression. I fit into a smaller size, however muffin-topped they made me, but I knew they would constantly be stuck on my calves4, which would require regular bending and adjusting, especially when standing up.

In order to avoid that discomfort, I went a size up. Comfortable, sure, but now I wonder if the pants aren’t a bit too baggy. You take that bagginess, and make them a bit too short (blame the tailors at the nameless store from which I purchased them), and suddenly your bottom half has stepped out of the ‘90s, but not in the cool way.5

A Brief, Frightening History of Style Misses

This almost-but-not-quite aspect of my pants epitomizes my greatest sartorial6 fear: getting close, but not nailing it. When I try to figure out when and where that fear was born, the little workers in my mind come back from the archives with two memories.

First: When I was growing up, I didn’t care much for sports, but I did care about fitting in.  So, like every boy my age, I wanted a Starter jacket. You know the type: nylon pullovers emblazoned with a team logo.7 Only my parents couldn’t afford to buy me one. Instead, like something out of a Roch Carrier story,8 they bought me a denim bomber jacket with Blue Jays imagery pressed onto the back. It was a man’s jacket, much too big for my 10-year-old frame. I knew immediately that it was not cool (though, I wouldn’t mind having it now), certainly not as cool as a Starter jacket.

And of course, the big kids at the back of the bus also knew it wasn’t cool. And they let me know it.

Second: I gained weight in my last year of university. Quite a bit of it, actually. Only, unless you’re preparing for a dramatic turn in an Oscar bait performance that requires you to bravely put on fat, weight gain is pretty subtle. As such, I didn’t realize how big I got until I saw a photo of me posted on Facebook. It changed my life. Not only did it prompt me to stop eating so many pastries and nachos, I realized that one can transform from a beauty to a beast without knowing it. One must always be suspicious of how one looks.

There are other memories, too, less remarkable but still convincing: you are never safe. Misplaced confidence in one’s style can happen to anybody. Just look at denim-tux-clad Justin Timberlake, or Ben Affleck’s back tattoo, or your own father. Fashion magazines often claim that we live in a postmodern era where rules no longer apply. This is patently false, of course. What they mean is there is no one look to have. You can dabble in streetwear on Monday and rock a suit on Wednesday (which, you’ll recall, is the day of the week Craig David begins making love) then finish off the week in, like, an all-white Batman costume.

But poorly tailored pants still look dumb. Overly baggy seats still make you look fat. Khakis—perhaps the most versatile pant—are still fraught with danger.

The Facts

Short pants are cool. Still somehow recovering from their brief tenure as the most taboo body part, ankles are feeling free again. People want to see them! So, it’s a win-win. If they aren’t too short, as my co-workers allege, then I’m just as cool as I would be if they were intentionally too short.

But that brings up the one bit of style cliché that is actually true: it’s less about what you wear, and more about how you feel wearing it. Note that I didn’t say it’s entirely how you feel wearing it. Comfort as the sole consideration is a philosophy that has brought us all dangerously close to a future ruled by athleisure brands.9 It’s all about finding that balance between comfort and confidence.

And in the end, that’s why these pants are too short. They feel like I’m wearing an auto-corrected text. You can tell what I’m going for, and it’s clear I tried, but something is not ducking right.

I need three more centimetres and I’d feel better. Or maybe some stirrups.

References   [ + ]

1. Let’s be real, the bottom button of a blazer is the appendix of menswear. Of course people make mistakes with it. There are very few things that are created for the sole purpose of not being used. It’s like Avada Kedavra for suiting.
2. Having been to exactly one bar mitzvah, I’ve realized the one rule you must follow: dress better than the kid singing out the Torah. It’s his day, but he still needs a reminder that clothes—not religious ceremony or sacred tradition—make the man. And he’s not there yet.
3. But if you want to, please contact St. Joseph Media.
4. My right one especially. Apparently, when I run, I only use my right leg?
5. Although, to be fair, these khakis are neither pleated, nor especially wide-legged. And it’s not like short pants was a problem in the ’90s. If anything, they had far too much pant bunched around their ankles. But, I feel like I’m wearing Chandler Pants.
6. Just a note of a apology: I hate the word “sartorial,” too. But I’m also grateful for it whenever I write about style. There are only so many synonyms available.
7. If my school was any indication, the style of jacket was more important than the fandom it ostensibly represented. Either that, or there were a lot of Tampa Bay Lightning fans in Edmonton, AB in 1994.
8. The Hockey Sweater, specifically. What other Roch Carrier stories are there? I also could have dropped a W.O. Mitchell reference here, too. CANLIT REPRESENT! WHAT! 
9. A future that is probably inevitable, actually, if the documentary series Star Trek: The Next Generation is to be believed.