I Wanted to Be a Hippie When I Grew Up: A lifelong fascination with fashion history, and the freedom of dressing across time

I Wanted to Be a Hippie When I Grew Up: A lifelong fascination with fashion history, and the freedom of dressing across time

Becoming Many Things at Once

When I was growing up, what I wanted to be shifted depending on when you asked me. There was a period where I was immersed in community theater and convinced I would become an actress. I spent years on a dance team and imagined a future shaped by movement. I loved writing deeply enough to eventually pursue an MFA in creative writing, and for a long time I thought I might become a journalist. I loved singing. I loved drawing fashion sketches. I was equally captivated by human psychology and science, which led me to study psychology with a minor in biology.

There were many possible futures, and I believed in all of them.

But underneath every version of who I thought I might become, there was something quieter and more constant. No matter what I imagined for my life, I always wanted to be a hippie.

Dressing for Joy

My idea of being a hippie was never rooted in politics or protest, and it had nothing to do with psychedelic mythology. I loved the music, but what drew me in most was the clothing.

I was enamored by the silhouette of bell bottoms, which I still believe is one of the most flattering shapes for both men and women. I was drawn to symbols, especially those that carried optimism and friendship, and the peace sign felt like a visual shorthand for both. I loved floral imagery, the language of flower power, the way denim could be endlessly reinterpreted. Patchwork felt like storytelling through fragments. Tie dye was both an activity and an outcome I loved, each piece holding its own unpredictable composition of color.

There was a sense of freedom in that wardrobe that felt almost emotional. It represented joy without hesitation. Dressing for no reason other than happiness.

If you had asked me then what I wanted to be, I might have answered with any number of professions. But I would have said, without question, that I also wanted to be a hippie. It never felt separate from anything else I imagined for myself. I remember going out on errands with my mom, dressed in what I thought of as hippie clothing, and it never felt like a costume. It was simply how I wanted to exist in the world.

Learning History Through Clothing

My fascination was never limited to one era. It expanded outward into a love of historical dress that began, as it does, with American Girl.

Before I even knew about the dolls, I found the books. They became my first real introduction to history. I loved the stories, but I was equally captivated by the “Looking Back” sections at the end of each book, where historical context, imagery, and everyday details were laid out with the intention of teaching children about a past they probably aren’t yet learning in school. It was the first time I understood that history could be lived, worn, and felt.

Then came the paper dolls.

I had already developed a habit of cutting out paper dolls from Simplicity and McCall’s pattern books that my grandmother would bring home, something I wrote about in No Fabric Goes to Waste: On Using What the Work Leaves Behind. But the American Girl paper dolls became an entirely different kind of obsession. Each one represented a real girl living in the present, with a wardrobe that traced her ancestry across time and geography. Every outfit came with a story. Every detail meant something.

I memorized everything. Names, places, fabrics, meanings. I would ask my mom to quiz me, as if I were preparing for an exam that did not exist, simply because I wanted to hold onto every piece of it. It was not enough to admire the clothing. I needed to understand it.

Imagining the Past Into the Present

Around the same time, I found another unexpected source of history. When I was ten, my church handed out student Bibles, and while I was not particularly interested in the religious text itself, I was completely absorbed by the sections labeled “Life in Bible Times.” They described how people lived in ancient civilizations, what they wore, what they ate, how fabrics were made.

I would sit in church, turning the pages slowly, searching for those sections, absorbing every detail. My school was not yet teaching history in a way that satisfied my curiosity, so I built my own education from wherever I could find it.

Clothing became the thread that connected everything.

Even the objects around me became part of that imagined continuity. When my grandmother gave me an old wooden school desk, complete with a metal cup meant to hold an ink pot, I treated it as if it had carried me into another century. I insisted on using a pen with a feather, even if it was purely symbolic, pretending to dip it into ink that was never there. It was not about accuracy. It was about proximity, about feeling closer to a time I could not physically enter.

Time Periods, Not Costumes

This way of thinking shaped how I dressed.

When Halloween came around, I was less interested in characters and more interested in eras. I dressed as a hippie one year, though it barely felt like dressing up since I already owned the clothing. Another year, I went as what I called “Pioneer Times,” wearing a long floral dress from my everyday wardrobe and adding a bonnet my grandmother had sewn for me. I was not trying to disappear into another identity. I was trying to step into a moment in history.

Other years followed the same pattern. A mod look with a mini dress and tall boots. An exaggerated 1950s silhouette with a bouffant wig and cat eye sunglasses. Even outside of Halloween, this approach remained. My grandmother made me a pink satin poodle skirt, and I wore it constantly, pairing it with simple t shirts and saddle shoes, blending it into my daily life. It was never a costume. It was simply another way of dressing. I wrote more about that piece, and what it meant to me, in Dressing as Self-Expression: Clothing as Memory and Story, where I explored how certain garments begin to hold identity over time.

I never felt bound to one era. I moved between them freely, borrowing what I loved and leaving the rest behind.

Carrying Time Through Clothing

For a long time, I had the sense that I might have been born in the wrong time. Not because I wished to live through the realities of those eras, but because I felt drawn to their visual languages. Their silhouettes, their textures, their ways of expressing identity through clothing.

Over time, I realized that I did not need to belong to any one moment in order to engage with it.

Clothing allowed me to carry pieces of different eras into my present life. I could sit at a nineteenth century desk while wearing contemporary clothes. I could dress in a way that referenced the 1960s while reading about ancient civilizations. I could take elements from multiple histories and layer them together into something that felt entirely my own.

This is the story I continue to explore through my work. The idea that clothing does not need to replicate the past in order to honor it. That it does not need to become costume in order to carry meaning. You can borrow, reinterpret, and re-contextualize without fully stepping outside of your own life.

Fashion becomes a way of acknowledging what came before while still remaining present. A way of holding memory without being confined by it.

After all, a single addition can shift everything. A bonnet can carry a modern floral dress back a century. A silhouette can echo a decade. A print can hold a fragment of a different time.

Clothing can be removed, changed, reimagined. But what it holds, the references, the memories, the quiet gestures toward history, remains.

An Invitation

If this way of thinking about clothing resonates with you, I invite you to join the collectors list, where I share new journal entries, collection releases, and the evolving ideas behind House of Caswell.

You can explore pieces that reflect this dialogue between past and present, including the Adriana Printed Denim Jeans, the Carly Ensemble, and the Sophia Mock Neck Top, each designed to carry visual language across time while remaining grounded in the present.

Join the collectors list and continue the conversation.