I still have the photo from that awful eighth-grade dance – me standing awkwardly in the corner of the gym, wearing what I thought were the coolest pants ever created. High-waisted, pleated khakis that my mom had convinced me were “very sophisticated” and would make me look “just like the girls in Seventeen.” What they actually did was create a visual effect I can only describe as “human accordion.” My body looked like it was comprised of exactly two parts: an endless expanse of beige pleats and then, abruptly, my face.
I spent the night trying to hide behind the punch bowl while Jessica Miller swanned around in her low-rise flares, looking like her legs started at her armpits. That night, I made a solemn vow never to wear high-waisted, pleated pants again, a promise I kept faithfully for nearly fifteen years. Until last Tuesday.
There I was at the Proenza Schouler sample sale, rifling through racks with the kind of focused determination that only New Yorkers at sample sales possess, when I spotted them – high-waisted, wide-legged, deeply pleated trousers in a rich tobacco brown. My first instinct was revulsion, my brain immediately flashing back to that eighth-grade dance and the subsequent trauma. But something made me grab them anyway. Maybe it was the fabric (a drape so buttery it felt illegal), or maybe it was the fact that the woman next to me was eyeing them like they contained the secret to eternal youth.
“Those are incredible,” she said, with the sincerity of someone who has never experienced pleated-pants trauma. “They’ll make your legs look a mile long.”
I snorted. “These? They’re going to make me look like my great-uncle Herbert.”
She shook her head with the confidence of someone who definitely had at least three fashion week invites in her inbox. “Trust me. Try them on.”
In the chaotic communal dressing area, surrounded by women in various states of undress and desperation, I wiggled into the pants that represented everything I’d sworn to avoid. And then I looked in the mirror.
Holy. Shit.
My legs, which on a good day might be described as “present” but never “long,” suddenly seemed to start somewhere around my ribcage and continue straight down to the floor. The high waist created a long, unbroken line, while the pleats – those same pleats I’d cursed for years – actually skimmed over my hips instead of grabbing them in a death grip. The wide leg balanced everything out, creating a proportion that was less “eighth-grade disaster” and more “woman who definitely knows how to order wine in French.”
I bought the pants. Then I went home and researched pleated, wide-leg trousers until 3 AM, falling down an internet rabbit hole that led me to the conclusion that either I’ve been wrong about pants for my entire adult life, or the fashion industry is gaslighting us all. Possibly both.
Here’s what I discovered: these allegedly “ugly” pants – the high-waisted, pleated, wide-leg trousers that spent years banished to the land of fashion don’ts – are actually secret leg-lengthening weapons. And not just for the six-foot-tall models who don’t need any help in that department, but for regular humans with regular legs.
The science behind it is surprisingly logical, even for an industry that once tried to convince us that tiny sunglasses that protect approximately 12% of your eye area were a good idea. High-waisted pants visually extend your lower half by starting the “leg line” higher on your torso. When those pants also happen to be wide-legged, they create a continuous, unbroken vertical line from high waist to floor. Your actual legs become almost irrelevant – it’s all about the illusion.
The pleats, which I had previously filed under “things that add visual volume exactly where I don’t want it,” actually serve a crucial function when done correctly. Rather than creating that dreaded pouchy effect at the hips, properly positioned pleats create movement and dimension that distracts from any areas you might prefer not to highlight. It’s optical illusion dressing at its finest.
I took my revelation pants (as I’ve come to call them) out for a test run the following week at a gallery opening in Chelsea. I paired them with a fitted black bodysuit, chunky loafers, and enormous confidence that I was sure would evaporate the minute someone looked at me with pity. Instead, I received three compliments before I’d even found the free wine. One particularly elegant woman in her sixties cornered me by a questionable installation of what appeared to be garbage arranged artfully on the floor.
“Those pants,” she said, gesturing with her champagne flute, “are exactly what women should be wearing instead of those horrible skinny things that cut off circulation.”
I wanted to hug her, but settled for asking where she shopped instead.
What followed was a complete wardrobe revolution. I now own five pairs of what I’ve started calling “leg pants” – high-waisted, generously pleated, wide-legged trousers in various fabrics and colors. There’s the original tobacco brown Proenza pair, navy wool ones from a vintage store in Greenpoint that used to belong to someone’s stylish grandmother, black linen ones for summer that make swishing noises when I walk, forest green corduroys that prompted my ex to do a double-take when I ran into him at Whole Foods, and cream silk ones that require me to avoid all liquids, foods, and possibly air while wearing them.
The revelation has caused me to completely reconsider other “ugly” fashion trends I’ve dismissed over the years. Those oversized blazers that I thought made everyone look like they were playing dress-up in their dad’s closet? Turns out they create a perfect counterbalance to high-waisted pants, creating a proportional harmony that’s more appealing than the fitted-everything look I’d been clinging to. Chunky loafers that I dismissed as orthopedic-adjacent? They actually ground a wide-leg pant perfectly, creating a solid visual endpoint that works way better than a delicate shoe that gets lost under all that fabric.
Even my mother – she of the “sophisticated” eighth-grade dance pants suggestion – has been vindicated. “I told you those pants looked good,” she said smugly when I FaceTimed her in my revelation pants. “You should listen to your mother more often.”
“Those pants made me look like a sentient paper bag,” I reminded her.
“Well, yes,” she admitted. “But the concept was sound. The execution was just… early 2000s.”
She’s not wrong. Context matters in fashion. The high-waisted, pleated disaster pants of my youth were made of stiff khaki cotton with no drape, cut straight through the hip and thigh, and paired with baby tees that created a proportion so bizarre it should have been studied by scientists. Today’s version – with its fluid fabrics, thoughtful proportions, and balanced styling – is an entirely different animal.
What’s most interesting to me about this trend revival isn’t just that these pants are back, but that their entire reputation has been rehabilitated. What was once considered the least flattering silhouette imaginable is now recognized as leg-lengthening magic. It’s a reminder that so much of what we consider “flattering” is just whatever we’ve most recently been told is flattering.
I tested this theory last weekend at a brunch with friends, wearing my navy revelations with a slim turtleneck and gold hoops. Emma, who has known me since college and witnessed firsthand my previous pleated pants trauma, stopped mid-mimosa.
“What is happening? Your legs look ridiculous right now. Like, in a good way.”
I explained my leg pants revelation, and by the end of brunch, we’d made plans for a shopping expedition to find her some too. When a woman who once described pleated pants as “the devil’s work” is voluntarily shopping for them, you know something significant has shifted.
For anyone tempted to try this trend but still scarred by pleated pants of the past, here’s what I’ve learned: fabric matters enormously (look for something with movement and drape), the pleats should lie flat at the top rather than poofing out immediately, and the waistband should hit at your actual waist – not your lower ribs, not your belly button, but that sweet spot in between.
Most importantly, wear them like you mean it. Nothing kills a potentially great fashion moment faster than looking like you’re not sure if you should be wearing it. The confidence to rock allegedly “ugly” fashion often makes the difference between looking fashion-forward and looking like you got dressed in the dark.
So here I am, twenty years after that awful dance, standing in front of my mirror in pleated, high-waisted pants, looking like someone with the proportions of a gazelle rather than an accordion. If Jessica Miller could see me now, she’d definitely want to know where I got these pants. And unlike eighth-grade me, hiding behind the punch bowl and wishing for different pants, I’d tell her – right after I reminded her about that time she spilled fruit punch all over her “perfect” flares.
