No One Understands the Struggle of Finding Comfortable Jeans More Than I Do

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Jonathan Borge - Lead
Photo: Kyleen James

Jeans are inherently suffocating. I know this from my 25 years spent inside of them, and I know this because, according to Merriam-Webster, to suffocate is “to make uncomfortable by want of fresh air.” And yep, my thighs, uncharacteristically thick and round by European size-chart standards, kill for a refreshing dose of oxygen each time they spend a day inside of my tight-ass Acne Studios jeans, a pair of dark-wash, not-so-often-worn denim puppies that cost me more than $200 and hours of emotional distress in front of the mirror.

Here’s the thing. I grew up as an overweight kid (“Obese!” my doctor once proclaimed) with less confidence than an average 16-year-old, an unwavering addiction to Zebra Cakes, and a Nicaraguan family who still doesn’t see the harm in loading up on churrasco, red beans, and buttery rice every. single. night. My relationship with pants, more so jeans, is deeply rooted in negativity.

Each August, when it was time to shop for a polished, off-the-shelf uniform (elementary school regulation called for Dickies-like khakis, though I then preferred something from Old Navy or Gap), my mother would worrisomely remind me of just how much weight I’d gained that summer. “Wow. This size doesn’t fit anymore. We have to try Husky,” she’d say as we both did our best to squeeze my way into threateningly tight pants that no longer fit the dimensions my body carved a year earlier. I’d moan, I’d groan, I’d cry. I’d size-up, and then I’d go home to make myself feel better with more sugary, late-night carbs. A bowl of Fruit Loops at 1 a.m.? Sign me up for thirds. At one point in junior high, I was wearing a size 42. For adult men.

Fast forward a decade, a prayer, and lots of time spent on the treadmill later (phew!), and I’m thankfully a healthy, active size 32 with a love of style but a serious aversion to trying on new pants. My solution is found in elastic waistbands, joggers, and anything that paves the way for the mercy of breathing room. Bow down to the fashion gods for the reemergence of ‘90s band tees (we have Justin Bieber and Kanye West to thank for that, too) and the acceptance (sort of) of wearing athleisure-inspired looks at a cocktail event. I know, I know, it’s been such a long time since Vetements gifted us with Champion logo-colored sweatpants (spring 2016, to be exact), but I’ll excuse my affinity for recreating the look as capital F fashion for as long as I can.

Perhaps the answer to finding the perfect pair of jeans is found in a tailor, but why should picking some up off the shelf be so challenging? Two years ago, I said, “Enough is enough!” I likely didn’t mouth those precise words, but I did drag my uber patient boyfriend with me to Barneys New York on a quest in search of the perfect jean.

I hit up the contemporary floor, buddied up with a friendly sales guy, and tried on e-v-e-r-y-t-h-i-n-g. I told him I had no price point, though, let’s be real, any pair above $200 isn’t worth it in my book. And that’s not to say those are affordable. The part of me that thinks I live in Ryan Gosling’s body dared to try on a skinny black Saint Laurent pair. Now that’s a fashion joke if I’ve ever heard one.

Nothing honestly fit comfortably, so we then headed downtown to Soho, where we frustratingly sifted through shelves of Acne, Joe’s Jeans, Bloomingdales, Zara, J.Crew, and every other store in sight for something I felt good in. Joe’s worked (below).

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Kyleen James

I learned that there are four denim styles that do get the job done. My absolute go-tos are my all-black Super Slim Joe’s Jeans pair(s). I don’t even think they’re in production anymore, and I’ve worn mine so often that they’ve been tailored, ripped, patched, re-patched, and put through the ringer. They day they rip harshly will be the day I give up.

In conducting “research” for this story, I discovered I also don’t mind wearing Levi’s 511 slim-fit Selvedge jeans ($128; A new pair to add to the rotation. Score!

Then we have my Club Monaco Slim-Fit Jean Bleach Tint pair ($100;, a cute, light-wash version that make me feel like Britney Spears in her “Sometimes” music video. They’re comfortable, but at times feel like cardboard.

Speaking of cardboard, my Acne Studios Spaniel Vintage medium blue pair ($109; are, well, fine. And by fine, I mean the fine you tell you’re boyfriend when you’re actually pissed. They hug my thighs precisely, require a little bit of cuff action, and then, like a lot of pants I try on, do that thing where they squeeze at the hips but leave way too much room at the waist.

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Kyleen James

My relationship with jeans today is a tumultuous one. On paper, I love denim. Who doesn’t? Refusing to wear America’s favorite textile on rotation is purely unpatriotic, right? Wrong, wrong, wrong! I roll my eyes at the thought of trying on a new pair inside a store. And should you need me to squeeze my booty (it’s larger than your average dude’s, just sayin’) into a pair that’s fresh-out-of-the-drier, prepare for me to have more sass than Gigi Hadid at the 2016 AMAs.

The various, creative ways in which denim styles are labeled don’t help my cause, either. Names like “Slim-Fit,” “Super-Skinny,” and even “Straight-Leg” imply that all men are created equal. Guess what, we’re not. Some of us have shapelier proportions and actually look forward to leg day at the gym. What, exactly, does “regular” fit mean? Am I less regular than the guy (aka, model) who can easily slip into a slimmer pair? Why isn’t there a label that reads, “Tight at the thighs, tailored throughout, room for the butt, feels comfortable”?

Maybe Khloé Kardashian was onto something when she labeled the three styles found in her new denim line, Good American. They’re called “Good Legs,” “Good Cuts,” and “Good Waist,” and I’d surely gravitate more towards one of those three than anything prefaced with the word “skinny.”

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So how did icons of style like James Dean, Steve McQueen, and Freddie Mercury make it look so easy? I wish I knew the answer. What I do know is that you can’t knock it ‘til you try it, which is why I’ll keep sweating and swearing my way from one fitting room to the next until I one day find a pair that fits like a glove.

In the meantime, you’ll find me gleefully enjoying the space my elastic-waist joggers provide. I stocked up on Black Friday.

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