An Interview with Gallerist Skye Weinglass

A woman wearing a black top stands in an art gallery filled with colorful works
Skye Weinglass at Skye Gallery Aspen in New York City. Courtesy Skye Gallery

Aspen’s outsized presence in the cultural consciousness and billionaire appeal belies the fact that it’s actually a pretty small town. The caveat being that it’s a small town developed under the guiding hands of Elizabeth and Walter Paepcke, who saw its potential to attract thinkers and creators. Today, along with luxe skiing, music and film festivals, lavish accommodations and a thriving culinary culture, it boasts an active art scene. There’s the Aspen Art Museum (with its annual Art Crush gala), the Red Brick Center for the Arts and Anderson Ranch Arts Center, along with several art galleries and a program of art in unexpected places.

This is where Skye Weinglass, owner of Skye Gallery in Chelsea, grew up—specifically in the legendary Merry-GoRound Ranch owned by prominent philanthropist and retail entrepreneur Leonard “Boogie” Weinglass. An artist herself, Weinglass studied painting and printmaking in college before studying studio art in Florence, Italy and Guadalajara, Mexico. In 2017, she made her mark on the Aspen art scene with Skye Gallery, a female-led and artist-centered space that hosted a year-round schedule of exhibitions plus workshops, pop-ups and performances.

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But after seven successful years contributing to the cultural community in Aspen, skyrocketing rents forced the gallerist to close up shop and think about next steps. Weinglass ultimately relocated the gallery to New York City in the fall of 2023, creating a space that’s still very much grounded in her Aspen roots. So far, Skye Gallery has mounted two group shows in the new space in High Line Nine, with a third now on view:  “eye candy,” which delivers on its promise. Vibrant works by Alexis Nunnelly, Anna Ortiz, Daniel Freaker, Dina Nur Satti, Emma Childs, Esther Ruiz and Tamara “Solem” Al-Issa form an absolute riot of color that invites viewers to delve more deeply into the artists’ stories.

An abstract painting in shades of blue and maroon hanging on a white wall
Emma Childs, ‘The Commonality #2,’ 2023, Acrylic on Canvas, 60x72in. Courtesy Skye Gallery

Observer recently caught up with Weinglass to chat about her move to the Big Apple, supporting underrepresented talent and what’s changed since decamping for Chelsea.

What brought you from Aspen to New York City?

I’ve always felt a strong pull toward New York City and have dreamed of living here. I used to see Broadway plays annually for my dad’s birthday and I remember getting a surge of excitement and inspiration the moment the flight would land. Coming from a small town, I’ve always dreamed of living in a dynamic city surrounded by a diverse range of people and cultures different from myself.

When I first opened Skye Gallery in Aspen, I had no intention of staying as long as I did, but the gallery quickly grew into a success so I stayed put longer than planned. We were able to cultivate a thriving art and community space in the heart of Aspen for years.

When my rent tripled after the world fled to Aspen during the pandemic, I was forced to close in 2022 alongside many other local Aspen businesses. I was heartbroken at the time but eventually felt grateful for the opportunities that opened up afterward, like opening a new gallery in New York! It has been a full-spectrum experience opening our new space in NYC this past fall—very challenging yet inspiring.

A pink hued painting of a staircase surrounded by greenery
Daniel Freaker, ‘Dawn Ascent,’ 2023, Acrylic on Canvas, 43.30×35.40in. Courtesy Skye Gallery

Do you have any thoughts on the differences between the two markets?

In Aspen, the gallery was a fun community hub amidst a fine art gallery, and we’re bringing a touch of that Aspen flair to Chelsea. My focus continues to remain on local artists. While in Aspen, we primarily showed a wide range of Colorado-based artists. In New York, we are tapping into the extensive and vast sea of talent throughout Brooklyn, Manhattan and on the East Coast.

In addition to selling wonderful art, building a vibrant and inclusive community is at the heart of my vision for Skye Gallery. We’re starting to see a growing community bloom here in New York. We’ve created a new team and expanded our community through artist talks, music events, fashion popups, jewelry trunk shows, dinners and more.

In Aspen, you wanted to provide space for artists who might otherwise be underrepresented. Are you doing the same in New York?

Supporting underrepresented artists has always been and will always be a core pillar of the Skye Gallery mission. I’ve always tried to provide a platform for artists, especially in the exclusive contemporary art world. One of our main goals is to provide a space for artists who deserve it and who may be overlooked in more traditional galleries. With the infinite artistic talent New York has to offer, I am taking the time to meet many different artists and I am excited to continue and to see that my search has exponentially expanded since moving from a small town to a big city.

You’re an artist as well as a gallerist. How has your experience as a creator influenced which artists you choose to represent?

My background as a painter and printmaker has certainly helped me to seek and identify the genuine artists out there who are truly dedicated to their work, those who are masters of their craft, more so than those who just have a name in the art world. Authenticity paired with talent is what I look for.

Tell me about the gallerists (or artists) who’ve inspired you—what is it about them in particular that motivates you?

I opened my first gallery pop-up at age 26 to support local artists. At that time, my art community was more friends or friends of friends, so I opened the gallery inspired by those artists around me. I had not yet tapped into the broader art world. That was another huge reason why I chose to open the gallery in Aspen—to support emerging contemporary artists in a town that would support their art career by supplying clients to buy their work. There weren’t many contemporary art galleries in Aspen at the time, and I saw a real need to support the many local and genuine artists existing without representation. When I opened the gallery there weren’t many other gallerists doing the same thing, which allowed me to be more experimental and flexible with my gallery. I’ve always chosen artists based on my intuition and interest in their work. Now that I’m in the New York market I can start learning from and pulling inspiration from other galleries and their unique programming.

A blue hued painting of a nude woman on a hammock
Alexis Nunnelly, ‘Gravity,’ 2020, Acrylic on Canvas, 68x50in. Courtesy Skye Gallery

As a gallerist dedicated to promoting genuine and thought-provoking artwork, Spencer Hansen’s work serves as a constant source of innovation and inspiration. What sets Spencer Hansen apart is his unwavering commitment to creativity and authenticity. He’s the most dedicated artist that I’ve had the pleasure of spending time with; furthermore, he creates very unique and compelling work.

Each of his creatures feels like a journey into an imaginative world. Whether he’s sculpting a human-sized resemblance of a peaceful bat or he’s creating a family of “Mochi’s” that resemble otherworldly and playful fur creatures, he really brings his sculptures to life. When you step foot into the gallery, it feels like you’re entering another planet. His masterful attention to detail is unrivaled in the hand-carved woodwork and hand-sculpted ceramic juxtaposed with the repurposed fur and material. Hansen’s work is meticulously clean yet playfully inventive. Skye Gallery is honored to host his fifth solo exhibition this Spring!

What advice would you give someone looking to follow in your footsteps?

Keep going, and don’t get discouraged. The art sales always ebb and flow. Stay committed to the mission of supporting artists and don’t get sidetracked or discouraged by the politics of the art world (at least this is what I tell myself). If the mission is to support artists, there will always be an abundance of help.

A deep blue amphora rests on a white pedestal
Tamara Solem Al-Issa, ‘Round Amphora,’ 2023, Stoneware, cobalt blue, clear glaze, 15x9x9in. Courtesy Skye Gallery

Gallerist Skye Weinglass Is Bringing the Best of the Aspen Art Scene to NYC

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