So there I was, standing in our tiny office kitchen making my third cup of coffee at 10 AM when our newest intern walked in wearing what I can only describe as… a lot. Like, a tennis skirt over baggy jeans, a cropped graphic tee layered under an oversized flannel, chunky dad sneakers, and – I kid you not – a knit beanie. It was July in Portland. It was already 75 degrees and climbing.
“Morning!” she chirped, completely unbothered by my obvious staring. I managed a weak “hey” while my brain tried to process what I was looking at. Was this a mistake? A dare? Some kind of performance art piece about climate confusion?
“Love your… outfit,” I said, immediately cringing at how much I sounded like my mom when she was trying to be supportive of my questionable fashion choices in high school. The intern – Emma, I think? – beamed at me. “Thanks! I’m going for chaotic balletcore meets blokecore today. Very intentionally unhinged.”
I nodded like I totally knew what blokecore was while making a mental note to Google it the second she left. Spoiler alert: it’s apparently when you dress like a British football fan from the ’90s, which explains absolutely nothing about the tennis skirt situation.
That interaction sent me down a rabbit hole that’s honestly changed how I think about getting dressed. Because here’s the thing – I’ve been low-key judging Gen Z’s fashion choices for months now without really understanding what they’re doing. And it turns out what they’re doing is actually kind of brilliant, even if it makes zero sense to my millennial brain.
You know how we grew up with shows like “What Not to Wear” basically drilling into our heads that there were RIGHT and WRONG ways to get dressed? Don’t mix prints, create a flattering silhouette, follow the “rules” of proportion? I absorbed all of that so deeply that I still catch myself doing the thing where you hold different tops up to your body in the mirror trying to figure out which one makes you look “better.” Whatever that even means.
But Gen Z didn’t grow up with Stacy London telling them their outfit choices were crimes against fashion. They grew up with TikTok algorithms serving them visual inspiration from literally everywhere – K-pop stars, anime characters, random teenagers in bedrooms, vintage fashion accounts, gaming aesthetics. No context, no rules, just endless possibilities. When your fashion education comes from an app that shows you 200 different aesthetics before breakfast, of course you’re going to approach getting dressed differently.
The trend that’s been breaking my brain is this whole “chaotic layering” thing. It’s exactly what it sounds like – deliberately mixing pieces that shouldn’t go together in ways that create visual tension. Dresses over jeans. Multiple tops layered in unexpected ways. Sporty pieces with feminine pieces with alternative pieces all at once. It looks random, but I’ve started to realize it’s actually incredibly calculated.
I decided I needed to understand this better, so I asked Emma if she’d explain her process to me over lunch. We went to this salad place downtown (some things really are universal across generations), and she basically gave me a masterclass in intentional chaos.
“The whole point is that it’s not supposed to make immediate sense,” she told me, stabbing at her quinoa bowl. “Like, if my mom looks at my outfit and thinks it’s cute and normal, I know I’ve failed.” When I asked how she actually puts outfits together, she shrugged. “I usually start with one piece I really love, then I add things that create tension with it. So if I’m wearing something super girly, I’ll throw on something masculine or sporty. If something’s fitted, I’ll layer something oversized over it.”
The word “tension” stuck with me. That’s design vocabulary – creating visual interest through contrast and unexpected elements. I use the same principle when I’m working on logos or layouts. Why hadn’t I thought about applying it to clothes?
Here’s where I probably should have just appreciated this insight from afar and gone back to my safe uniform of jeans and nice tops. But apparently I have zero self-preservation instincts when it comes to fashion experiments, because I decided to try chaotic layering myself.
I started small – just layering a vintage band tee under a slip dress with combat boots. It felt weird but not totally ridiculous. Then I got bolder. I wore a prairie dress over straight-leg jeans with a cropped cardigan and platform sandals. Added some layered necklaces that definitely didn’t match. The whole thing should have looked like I got dressed in a tornado, but somehow… it worked?
The reactions were fascinating. My coworkers (all millennials) kept giving me these concerned looks like maybe I was having some kind of breakdown. Sarah literally asked if everything was okay at home. But the younger people in our building? They were into it. The barista at the coffee shop downstairs complimented my “fit.” A teenager waiting for the bus gave me an approving nod.
I kept experimenting for about a week, and honestly? It was the most fun I’ve had getting dressed in years. There’s something incredibly freeing about deliberately breaking all the rules you’ve internalized about “flattering” dressing. When you layer a babydoll dress over wide-leg pants with chunky sneakers and somehow don’t look like a complete disaster, you start questioning what other fashion rules are just arbitrary nonsense.
The millennial approach to style has always been about finding your “signature look” and then sticking with it. We’re the generation of capsule wardrobes and investment pieces and spending hours researching the perfect white button-down. There’s nothing wrong with that – I still think everyone should own at least one really good blazer. But it assumes style is this fixed thing you discover once and then maintain forever.
Gen Z completely rejects that idea. Emma has a different aesthetic every single day. Monday she’s cottagecore, Tuesday she’s cyber-goth, Wednesday she’s normcore. It’s not indecision – it’s intentional exploration. For them, fashion isn’t about finding your look, it’s about using clothes as creative expression that changes with your mood, your influences, whatever you’re consuming on social media that week.
But here’s what really got me: when I asked Emma if she worried about whether her outfits were flattering, she looked genuinely confused. “I mean, I like how I look,” she said. “But I’m not really trying to look conventionally attractive or whatever.” The freedom in that statement honestly made me a little jealous. How much mental energy have I wasted over the years worrying about whether something made me look thinner or gave me a better silhouette?
I’m not saying I’m going to start wearing beanies in summer or layering tennis skirts over everything (my millennial neuroses run too deep for that level of chaos). But incorporating some of this mindset has been genuinely refreshing. Last week I wore a slip dress over jeans to a networking event, finished with platform loafers instead of the heels I would normally wear. When someone asked why I was dressed “like that,” I found myself channeling Emma’s energy: “Because it’s more interesting this way.”
And you know what? It really was more interesting. I felt more like myself than I had in months of playing it safe with “appropriate” outfits.
The generational style divide isn’t going anywhere. Gen Z is going to keep confusing the hell out of millennials with their seemingly random combinations, while we clutch our skinny jeans with increasing desperation. But maybe instead of side-eyeing teenagers in leg warmers and mini dresses, we could learn something from their approach.
Not necessarily copying the specific aesthetic – I’m probably never going to be cool enough to pull off true chaotic layering. But embracing the freedom it represents? The idea that fashion should be fun and experimental rather than about following rules someone else made up? That getting dressed can be creative expression rather than just trying to look “appropriate”?
I keep thinking about how horrified my mom was by my low-rise jeans and chunky highlights in 2003. Fashion has always been about younger generations confusing older ones. The only difference now is that the cycles are faster, the combinations are weirder, and thanks to social media we’re all watching it happen in real time.
So the next time you see a teenager wearing what looks like three different decades of fashion simultaneously, remember – they’re not confused about getting dressed. They’re just brave enough to wear exactly what makes them feel something, whether the rest of us understand it or not. And honestly? That confidence might be the most stylish thing of all.
Madison’s a Portland-based designer who treats thrift stores like treasure hunts. She writes about dressing well on a real salary—think smart buys, affordable finds, and brutal honesty about what’s worth it. Stylish, broke, and proud of it.
