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Conversations with Kelsy Osterman

Today we’d like to introduce you to Kelsy Osterman.

Hi Kelsy, please kick things off for us with an introduction to yourself and your story.
My story in the world of hair has touched many sides of the industry. It began at the Aveda Institute, followed by advanced training at Juut Salon, and then a move to New York City in 2009 where I joined Cutler Salon. Rodney Cutler, the Australian owner, sponsored artists from around the world, and I found myself surrounded by incredible international talent.

I dove into Fashion Week, worked editorially with artists like Peter Gray, and styled celebrities such as Courtney Love and Gwyneth Paltrow. I loved the creative energy, but not the eighteen-hour days where wellbeing was the last thing on anyone’s mind.

Eventually I stepped away from that world and picked up my own camera, capturing hair in environments that felt more soulful and true to me. Hair became my art form.

After a decade with Spoke & Weal—where I honed my craft in dry cutting, worked within an incredible community of strong leadership, and experienced high-end opportunities for growth—I moved back to Minnesota part-time in 2020 to help open their ninth location.

In early 2025 I stepped fully into business ownership and opened The Salon by Kelsy, a one-chair salon inspired by the French artist salon movement. It’s a space where hair, nature, and art come together in a living expression of intelligence, beauty, and connection.

A dream I carried for years is now my reality, one I’m honored to share with others

We all face challenges, but looking back would you describe it as a relatively smooth road?
My road has been steady and focused. I’ve given my whole self to my craft, which over time has become my art. Moving to New York City was one of the best things I ever did. It allowed me to try everything on. I hustled, got gritty, and gathered a lot of wisdom from living such a focused, driven life.

The real struggles, I think, are life itself and the lessons we are all meant to learn along the way. Depression and heartache were part of my story too, but I moved through them and came out the other side. What carries me forward is curiosity, beauty, and connection. That is where I always find my center.

Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
I am a hairstylist by trade, living every day as an artist. Not every stylist leads with this kind of lifestyle. I live and breathe my work, taking in the world around me, noticing the details that make things beautiful, that hold ease in their being, that show us what it takes to transform and break free. Life is a sensory and aesthetic journey, and that is how I see hair.

Hair is a living fiber that travels with us through life. It is a companion, a teacher, and at times, an enemy. It is a gateway to healing, sending messages from within. It is soulful and aesthetic, deep and surface, beautiful and challenging.

Aesthetics are the foundation of my work, not in the superficial sense, but as a language of harmony, proportion, and feeling. I see myself as a guide, helping people live in their hair with ease and coolness. Whether behind the chair or on set, I ask questions that invite clients to connect more deeply to what they are really asking for. I cut hair dry, in its natural state, fascinated by how it moves like trees in the wind, creating natural shape. I crave hair instead of just cutting it. I sculpt it to move with the person. It is a dance.

Hair is my mother medium, and the person it belongs to is the muse that brings the sculpture to life. I am proud of my journey and love where I have landed in my artistry and career. It has taken twenty-four years to arrive at a place that feels both dreamy and real.

Sculpting hair in a nature-held, light-filled space with groovy music, curated scent, and calm energy, the whole sensory feels at peace and deeply inspiring. My approach is unique, rooted in movement, beauty, and wellbeing. I hope to continue attracting like-minded artists and collaborators who value artistry, connection, and the quiet power of aesthetic intelligence.

That is what sets my work apart — it is alive, intentional, and deeply felt.

Where we are in life is often partly because of others. Who/what else deserves credit for how your story turned out?
I have had so many important people in my life who have helped me along the way.

Margret Menke was there at the beginning. She was my consultation and aesthetic educator. She embodied such beauty and so generously shared her intelligence with me.

Rodney Cutler took a chance on me, a Minnesota stylist who wanted to take a shot at the big city. He asked me what my dreams were and how he could help make them happen.

Jon Reyman saw my individuality and perspective and always left room for my ideas at the table. He helped me get clear on my path, asking big questions that pushed me to find my own answers.

Liz Norton, co-owner of Spoke & Weal, is one of the most impeccably intelligent and creative women I know. She leads with her heart, her artistry of service, and her incredible capacity for intensity and grit. She never gives up.

Christine Thompson, co-owner of Spoke & Weal, a master colorist and visionary, taught by example in the most profound way. She leads with an open heart and mind, and the way she shares her intelligence is a gift to the world.

Constance Walsh is a wise woman I met in the desert over a decade ago. She has lived many lives and now calls Joshua Tree home. She has been a constant support in my journey of mind, body, and spirit.

Anna Lee, a multi-talented and magical woman, has been my creative coach for almost two decades. She has helped me build and actualize my dreams, understand my path, and cherish all of my parts along the way.

Emma Pittelko, my partner and my love, is at the heart center of my story. She is home, safety, comfort, and belonging.

My family has been a lifetime of loving support.

My community of creatives — wow.

And the Earth. My guide. My foundation.

All of it matters. Yoga, organic food, acupuncture, weight training, good shoes, foam rollers, clean products — it all adds up. It all keeps me vital, so I can continue to do the work I love.

Contact Info:

  • Email: [email protected]
  • Instagram: Kelsyosterman
  • Facebook: The Salon by Kelsy
  • Youtube: Kelsyosterman
  • Yelp: The Salon by Kelsy

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