A year ago today (!) I completed a 500-mile walk across Spain. For 30 days straight, my routine was the same: walk about 15 miles with everything I had on my back, hunt down some churros or ice cream, hand wash my clothes in whatever sink I could find, and then crash into bed. I had three pairs of underwear, two pairs of pants and three shirts. I slept in whatever was clean. I wasn't concerned with looking beautiful, stylish or cool. In fact, everyday I looked like an absolute dork. My outfit was chosen based on function and budget—I needed quick-drying pants, cushioned shoes, odor-resistant shirts, and a jacket that made me visible in twilight as I walked along dimly lit roads.
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It felt strange to shed any semblance of swagger—no fashionable clothing, my protective armor, not even styled hair or makeup. Carrying everything on your back each day makes you realize how quickly you want to lose it all. All that was left was my smile, framed by constantly chapped lips, and my personality laid bare for all to see.
By day five, I was desperate for something new to wear, anything to signal to anyone looking at me that I was cool, interesting, and not just a wandering dork with blotchy skin. Sometimes when I met someone, I was tempted to whip out an old photo like a proud parent and say, "Look! There’s proof I’m not the poor man’s Sporty Spice in real life!"
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On this walk, I decided not to document it for anyone but myself. First of all, I knew I’d look rough every day and didn’t want to be sharing any selfies of my filthy, fluorescent Patagucci Lululoser looking self. But I decided to be smug, so I claimed it was a “spiritual break” to go off grid. No social media, no performing, just my notebook and camera. It was really disorienting to not get any feedback. I was a little shocked by the echo of my own thoughts.
Day after day of walking, I stopped focusing on my clothes. I confronted the harsh truth that much of my life's decisions were fueled by an underlying pressure to constantly prove one way or another that I simply deserve to be here: whether it’s through looking good, professional achievement, social status, or conforming to perceived notions of "coolness." It wasn't until I stripped away the armor of external validation—clothes, likes, status signals, trendy establishments—that I truly confronted this relationship with myself.
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I realized I had generally been at the mercy of everyone else’s reactions. I would liquify my identity to anything external and sought validation through it, only to find that when it was no longer rewarding, cool, or respected, then what was I? I’d get frustrated and go back on the treadmill, endlessly chasing after the next thing, like a tree with no root system swaying side to side until it inevitably snaps. Years and years of following these societal norms pushed me to be moody, reactive, and immature — someone who was constantly seeking fulfillment through chasing either validation or big life changes or control through shiny material possessions, yet finding only an insatiable void that nothing seemed to fill.
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Honestly, once I became aware of this constant dialogue ping-ponging in my brain, it got really old, really fast. I decided to practice being nobody special. What if I could be content with myself exactly as I am, without needing to constantly appear cool, compare myself to others, or want to feel any different than right now? I tried radiating warmth towards myself before chasing coolness or acceptance. I realized that my fear of being “invisible” or “irrelevant” wasn’t as scary as I thought it would be—maybe leaning into it was actually a superpower.
I thought de-centering myself would make me feel like a total loser. We live in a "me, me, me" culture where people trample each other for the first dollar, the first and last word, the first place in line—as if there's a gold medal for being the biggest jerk. But oddly, de-centering myself didn’t make me feel less than; instead, it allowed me to be more truly comfortable in my own skin.
All the weight of needing to be or appear a certain way fell off my shoulders (unfortunately, the weight of the backpack was still there). Perhaps confidence isn’t something to be built; it's right under the surface when that heavy bulk of needing to be someone is lifted. Embracing being no one helped me feel authentic and confident, which, in my opinion, is way cooler than any expensive-looking sweater.
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Of course, I didn't stop loving clothes just because I took a long walk and ate my body weight in churros. I still want to look good and care about what people think. What I didn’t expect was to come back and find my preferences and relationship to fashion had really changed. I always thought my perspective would shift by reading more about clothes, buying more clothes, or thinking hard about styling—not by simply walking.
But something shifted when I became more comfortable with myself than I had been before. A spaciousness opened up and showed me that if I want to love fashion and keep up with what’s relevant, I’ll be perpetually stuck in a game rigged by money and capitalism. This industry is a profit machine, banking on the idea that those at the top dictate what's cool, desirable, and necessary, and if you don't comply, you risk being left out.
My desire to participate and stay connected is okay because it's about wanting to belong with others. And while I allow these totally natural feelings, I now see they aren’t always used for the outcome I actually want. I certainly won't be following these feelings to the cash register anymore. I know that I can’t manufacture a sustainable identity through purchases or achievements or status. I no longer identify with brands or possessions, even when I really love and enjoy them. It's every company's dream for us to do that, but it ultimately leads to losing our humanity.
It doesn’t mean I can’t ever enjoy buying or wearing anything! It means for me that material possessions (and even external achievements) don’t really equate to my confidence any more. They usually fail to bring me significant community, connection and meaning, especially when I chase them from a place of lack and not empowerment.
It's tough to do this, no doubt. I struggle all the time. The marketing game is fierce, and the players are relentless. I personally feel a glimmer of hope right now—I see many of us getting tired of this charade, even though we still love clothes and fashion. If you're feeling this fatigue, take heart: I think it’s a sign of your humanity, intact and kicking. It signals that something is truly off amidst relentless pushers of consumption, always hungry, always on the prowl. It's okay to find it fun at times and at others to resist. Instead of blaming myself or feeling wrong for not fitting into this world of consumption labeled as expression or worth, I've come to realize that perhaps it's that world that actually doesn't fit me.
The New “Cool Girl”
When I got home from my trip I felt pretty excited to dress in anything other than sweat wicking fabric. I revisited some of my old Pinterest boards labeled “Cool Girl” and realized just how many of them featured women in basic outfits like a t-shirt and jeans. I could wear those outfits too, but I wouldn’t look like them at all. These women were often rail thin with an icy vibe—they were very serious about being cool. I also realized I was pulling lots of inspiration from people who were generally always trying to get me to buy something.
It didn’t feel right anymore. I could sense the difference between authentic effortless (actually not giving a damn and being comfortable in my skin) and this manufactured effortless I had known before (aka people with a whole lot of money and a whole lot of time who get to look like they rolled out of bed) It really begs the question: who actually gets to be cool anyway?
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Is it mainly people who are conventionally attractive, thin, white, or rich? Coolness is an elusive concept without a universal definition, allowing everyone to have their own interpretation. Some people’s entire job is making sure you don’t remember that.
My perspective on being cool or relevant shifted so much after I stopped fixating on it, and now it feels basically meaningless. When I encounter someone I perceive as cool or stylish, I admire and get a thrill from them, but I also recognize that they are navigating the same flawed system as I am. I don’t need to look like them or anyone else.
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Daniel Schillinger said, “I channel-surf other brains before consulting my own.” I’d like to do this less often. But when the time comes to channel-surf someone’s brain? I want to be careful they align with my best interests and who I am. Women come in all shapes and sizes, and I honestly love them all—but a Pinterest board full of thin, white blondes will never be me.
Why not draw inspiration from women who might look more like me or even embody the behavior and feelings I aspire to? Does a “cool girl” seem like an overall lovely person? Does she embody the type of person I’d like to be? I find that my new idea of a “cool girl” doesn’t exude that icy, unattainable coolness anymore, but rather an accessible warmth. They don’t resist the inevitability of aging, they are highly self-aware, honest, kind. They know life is short and they can laugh at the absurdity of it all!
My cool girl faded with those dirty Smartwool socks and Hokas. Maybe she never even existed, and I’ve been clinging to her ghost.
After all, reddit tells me she is dead:
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So tell me, are you still chasing that elusive cool girl and what does she look like for you? Or is your idea of the cool girl dead? And who has replaced her?
🍒Total Rec
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I feel like you articulated exactly how I’ve been thinking recently (I’m on a restricted shopping mission, doing the rule of 5 challenge this year and it’s changing my thought patterns about fashion, shopping, etc). When I’m tempted by an ad or Instagram outfit, I ask myself “cute shirt or just a cute body?” Just like the image you posted, mostly its “cute body.” Feeling comfortable/confident in a t shirt and jeans is my new goal- it’s surprisingly difficult. Love this post and thank you for writing it!
This substack continues to be some of the best fashion writing on the internet. This spoke to my soul. I would love it if you published a reading list with books/articles/etc that inform your writing here.