Summary: The history of fashion shows every generation dressing against the last, and this article follows that pattern from 1960s army surplus to the Silicon Valley hoodie to today. By the end, you’ll see why dressing nicely now feels rebellious.
The usual telling of the history of fashion is a timeline of silhouette trends, with each decade’s look replacing the last. That timeline doesn’t explain camo pants that read as protest to one person and as outdoor gear to someone else. This article follows some of the fashion rebellion moments in our lifetimes, and what’s emerging now.
How the History of Fashion Rebellion Began With Army Surplus
Military surplus first became a civilian symbol of dissent in the 1960s, when I was an itty-bitty kid. Vietnam Veterans Against the War is documented as among the first protesters to wear recycled army clothing. Hippies in the United States adopted khaki or camouflage drill jackets and navy bell bottoms to denounce the war, and there was loads of cheap surplus (I’ve noticed there isn’t much cheap surplus in the surplus stores now). After World War II, surplus camouflage was also popular with hunters, and commercial imitations made one pattern known as Duck Hunter.
The Camo Pants That Read Two Ways
My husband was born in 1963, same as me, and as a teenager in the late 70s he wanted to wear camouflage. For him it was practical. He was out goofing around in the woods (maybe there was a bus, but back then we walked a lot farther to school than kids do now).
His mom was born in 1945, and she grew up when camo was associated with rebellion and protest. Now we almost see it as patriotic to wear camo, but back then I think it was the opposite. When she saw him in what he thought was just practical clothing, she thought he was being rebellious.
Those same pants had two ways of seeing them, and both had their reasons. Each viewer reads a garment against the years they grew up in and what they saw happening around her.
Silicon Valley and the Hoodie as Power
Fast forward a while to Mark Zuckerberg wearing a hoodie on the Facebook IPO roadshow in 2012. A famous securities analyst told Bloomberg TV it showed he didn’t care that much, and called it a mark of immaturity.
Zuckerberg’s own explanation, in a 2014 public Q&A, was that he wanted to make as few decisions as possible about anything except serving the community, like Steve Jobs and all kinds of people before him. He wanted his energy for the work he was there to do.
What he meant and what people saw were two different things. Some people read that dress-down hoodie and t-shirt as power: a person so important he doesn’t have to dress for anyone. I feel like that is where the idea that we should just wear athletic clothes everywhere came from, to a degree, and how it got popularized.
The Voice Telling Women to Dress Down
My mom was really stylish when I was little. This may be incidental, not a pattern, but she earned her master’s and a doctorate while I was a little older kid, and somehow I picked up the idea that she thought serious, intellectual, smart women don’t really bother with trying to look stylish.
Now that she’s retired, it almost feels to me like she doesn’t think she’s allowed to wear anything other than comfortable leisure clothes.
I think a lot of women have those kinds of questions in their minds. And the loudest voice saying that comfortable clothes are the only acceptable ones is coming from Silicon Valley. You know how people always say they want to be effortlessly chic? This is that effortlessly chic taken all the way: I don’t have to put any effort into it at all, and I’m super successful. That has sort of become a rule now, and a lot of people feel pressure to dress down.
What Does the History of Fashion Say About Dressing Nicely Today?
Rebellion is deviation from the default, so when casual rules, dressing nicely becomes the rebel move.
There’s a common belief that caring how you dress undercuts how intelligent or how successful you look. Rebellion is a deviation from what the majority group treats as the default.
I was in a doctor’s office the day I recorded this, and probably 20% of us were dressed in what we call hard pants, tailored pants. Nothing fancy, I was wearing cropped cords. Everybody else was wearing sweatpants or yoga pants, tech fleece, hoodies. I feel like people get questioned when they go out wearing something nicer than what people are expecting.
There’s nowhere left to go in terms of getting more casual and still being seen as dressed. The only way to go, for any of us, to deviate from the default in society, is up. In a casual room, dressing nicely gets noticed, and there’s pressure to return to baseline.
There have been some recent reports of buyers dressing with more purpose, leaning toward tailored coats and structured blazers, and of Gen Z at work reshaping formal wear with soft structure. I think these are early signs.
Why Deliberate Dress Gets Read as Status
Deliberateness changes how the same outfit gets read. Researchers Bellezza, Gino, and Keinan, in the Journal of Consumer Research in 2014, found that unintentional violations of dress norms can lead to negative inferences. If it looks like you accidentally did something wrong in your outfit, that is read negatively.
When the deviation appears deliberate, like wearing barefoot sneakers instead of high heels with your suit, it can lead to higher inferences of status and competence. People think you have enough autonomy to follow your own inclinations and bear the cost of deviating. It just has to look deliberate.
Finding the Deviations That Are Yours
To be deliberate, visual identity is looking and feeling like who you actually are, which I think is a priceless human right that frees mental energy for us to focus on our calling. When you align what you look like with who you are on the inside, that becomes a North Star for how you deviate from the norm and get respected for it.
I use a tool called Essential Aesthetic Images. It shows the themes your taste and preferences keep returning to. My working idea is that if a deviation echoes those themes, it reads as a pattern on you, which tells observers you know the norm and chose against it. A signature color palette and style framework gives you one coherent set of choices, so each deviation looks deliberate.
The Aesthetic Mirror & Palette Party is an online group experience where each participant brings one of her essential aesthetic images. It can be any image she loves, and I recommend against clothing: a photograph she took, a piece of art, a landscape, her favorite artist’s work. We share the picture with the group, and usually people come together with family members or close friends. The group shares the artistic themes they see in the picture, and it’s remarkable. Those themes always reflect the character qualities of the person who brought the picture. It’s super affirming, and then I help you see how to use that to inform your style. It also includes a seasonal energy palette, so it’s a really good deal.
What the History of Fashion Leaves Us With
Most people think the history of fashion is about trends, but it’s each generation defining itself against the last. Now dressing nicely feels rebellious.
Every outfit gets read against someone’s baseline, and a woman who dresses with intention gets read as someone who chose. When you are seen clearly, what you have to offer gets heard and used.
A Simple Project for This Week
Start a folder of images you love. Save whatever you find this week that resonates with your specific, individual idea of what beauty actually is.
If this article gave you a new way to read an outfit, applying it to the real clothes in your closet is a different task from understanding it. A free, collaborative Style System Synthesis call bridges that gap: we look at what you already know about yourself and figure out what’s missing. Book a free 30 minute conversation here whenever you’re ready.