I spent $200 on the ugliest jeans I’ve ever seen and now I can’t stop wearing them

Listen, I’m not someone who falls for weird fashion trends. My approach to denim is pretty straightforward – give me a pair of vintage Levi’s 501s that I’ve hunted down at some thrift store in Southeast Portland, and I’m happy. I’ve probably spent more weekend mornings than I care to admit digging through racks of questionable vintage pieces, looking for that perfect pair that’s been washed just enough times to feel like butter but not so much that they’re falling apart.

My entire denim collection has been curated through what I call the “real life test” – can I squat down to pet a dog without worrying about split seams? Do they look decent after an eight-hour day of sitting at my computer designing logos? Most importantly, do they make me look like I have some semblance of a shape instead of like I’m wearing a denim sack? These are the important questions.

So when these absolutely bizarre jeans started showing up all over my Instagram feed a few months ago, I was… not impressed. I’m talking about jeans with waistbands that went diagonal across your body, legs so wide they could double as tents, pockets placed in random spots like someone threw darts at a denim pattern. It looked like what would happen if you asked a three-year-old to design jeans while blindfolded.

“This is what happens when fashion people get too bored,” I texted my friend Sarah, along with a screenshot of jeans that honestly looked like they were wearing other jeans. “Like, who is the target customer for this?”

Turns out, literally everyone except me. My coworker Jake showed up to a client meeting wearing a pair with this weird crossover waistband situation that made it look like his jeans were trying to hug themselves, and when I gave him the look, he just shrugged.

“They’re actually way more comfortable than regular jeans,” he said. “The waistband doesn’t dig into your stomach when you sit all day.”

“They look like denim origami gone wrong,” I told him, which he somehow took as a compliment.

I was fully committed to my denim snobbery until I found myself at this Madewell press event – not because I’m fancy enough to get invited to press events, but because my friend who works in PR needed a plus-one and promised there would be free wine. Among all the normal, sensible jeans they had displayed, there was this one pair they were calling “offset jeans” that I kept… staring at.

The waistband was literally higher on one side than the other, creating this diagonal line across your torso, and instead of matching legs, one was wider than the other. They were objectively weird. They shouldn’t have worked. They looked like a mistake someone decided to call “design.”

But something about them kept pulling my attention. Maybe it was the actual denim – good weight, nice color, the kind of indigo that looks expensive even when it’s not. Or maybe I was just getting tired of wearing the same style of jeans I’d been wearing since college. When the PR person noticed me looking and casually mentioned they had my size, I figured… why not? Professional research, right?

The fitting area was basically a corner with a curtain that didn’t quite reach the floor, so I was fully expecting to hate how they looked and make a quick escape. Instead, I put them on and had this weird moment of… huh. They actually looked… good? The diagonal waistband thing that I thought would make me look like I was wearing a costume somehow made my proportions look more interesting. The mismatched legs balanced everything out in a way my perfectly symmetrical jeans never had.

I stood there in this makeshift dressing room, staring at myself in a mirror that was probably lying to me, trying to figure out if I was having some kind of fashion breakthrough or if the free wine was hitting harder than expected.

When I emerged from behind the curtain, walking like someone who wasn’t sure if they looked amazing or ridiculous, the PR person immediately pounced.

“They look so good on you!” she said, which is probably what they say to everyone, but still.

“I think I… like them?” I said, my voice doing that thing where it goes up at the end like I’m asking permission to have an opinion.

“They’re very editorial,” she added, which felt like fashion speak for “weird but in an intentional way.”

I walked out with the jeans, telling myself I’d wear them exactly once, confirm they were impractical for real life, and have material for a whole rant about ridiculous fashion trends. Except that’s not what happened at all.

The first time I wore them out was to meet friends for coffee, paired with the most boring white button-down I own because I figured conservative on top might balance out the chaos below. I felt so self-conscious walking down my street, convinced everyone was staring at my fashion identity crisis.

But then Marcus, the barista at my local coffee shop who’s never remembered my name despite me being there literally every morning for two years, looked up and said, “Oh damn, those jeans are fire.”

At coffee, my friend Lisa immediately wanted to know where I got them. “They make your regular jeans look so basic,” she said, which was both flattering and a brutal assessment of my carefully chosen denim collection.

By the third time I wore them, I was completely sold. I realized they actually worked with everything – black turtleneck and boots, basic white tee and sneakers, even blazers for when I needed to look somewhat professional. The jeans were doing all the visual heavy lifting, which meant getting dressed became easier, not harder.

The weirdest part was how versatile they turned out to be. Regular jeans have this very specific casual vibe, but these weird ones could shape-shift depending on what I paired them with. Flat sandals and a tank top for weekend errands, silk blouse and heels for dinner somewhere that uses real plates instead of paper ones. The unusual construction made them read as “design piece” rather than just “pants.”

Since then, I’ve gone completely down the rabbit hole. I now own jeans so wide they’re basically wearable architecture, a pair with a raw hem that looks like someone attacked them with scissors during a breakdown, and my latest acquisition – jeans with a seam that spirals around the leg like a denim barber pole. My beloved collection of vintage 501s is gathering dust while I explore what happens when people get creative with denim construction.

For anyone thinking about dipping their toe into weird jean territory, I’ve learned a few things that might make the transition less jarring. Start with one weird element instead of going full avant-garde. An unusual waistband is easier to ease into than jeans that look like they’ve been deconstructed and rebuilt by someone having an artistic episode.

Keep everything else simple when you’re testing them out. Let the jeans be the star and everything else be background players. I learned this the hard way when I tried to wear my spiral-seam jeans with a patterned top and looked like I was wearing a visual migraine.

Give them at least three wears before you decide. Weird jeans mess with your brain at first – what feels completely wrong on day one might feel genius by day three as your eyes adjust to seeing yourself differently.

Think about whether the weird element actually serves a purpose beyond looking different. My diagonal waistband isn’t just visually interesting – it’s genuinely more comfortable for all-day wear. Sometimes unconventional design actually solves problems you didn’t know regular jeans had.

There’s something psychological that happens when you wear obviously unusual clothes. I’ve noticed I carry myself differently in my weird jeans. There’s this confidence that comes from wearing something that’s clearly a deliberate choice rather than trying to blend in. Regular jeans say “don’t look at me.” Weird jeans say “yes, this was intentional.”

I’m not saying everyone should burn their normal denim and embrace the chaos. My vintage 501s still have their place, and they’ll probably outlast whatever weird phase I’m going through. But I am saying that my immediate rejection of unconventional denim was more about being comfortable with the familiar than any real assessment of whether they actually worked.

Sometimes the trends that make you roll your eyes the hardest end up completely changing how you think about getting dressed. Six months ago, I couldn’t imagine wearing jeans with a diagonal waistband. Now I can’t remember why that seemed so strange. Your fashion comfort zone expands in these little increments until suddenly what used to be weird becomes normal.

So if you see me around Portland wearing jeans that look like they’ve been through some kind of geometric transformation, just know I’m not having a quarter-life crisis or trying too hard to be cool.

I’m just a former denim purist who accidentally discovered that sometimes weird actually works better than normal.