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Artwork comes in many forms that resonates with people on different levels. It can evoke feelings in a way that words often cannot. This leads to our next artist that we are thrilled to share, as he captures this in a way that we haven’t seen elsewhere. Kai Sasaki is a designer of many talents, for he is an artist in addition to a shoe designer. What’s not to love about a multifaceted creator?!

Coming all the way from Fukuoka, Japan, Kai Sasaki moved to Hawaii 10 years ago during his freshman year in high school and went on to create the inspiring work that we see today. He mainly works on screen printing, canvas painting, and customizing shoes.

You can view his current works on Instagram @trippinarts.

Kai currently spends the majority of his time designing and customizing shoes due to the demand, and these are custom made for each individual commissioner. Curious about his shoe design process, he gave us the rundown:

“First, I digitally mock up and design the shoe. Then, make some final adjustments according to my commissioner's vision. Once we decide on the design, I prepare the surface of the shoes with acetone so the paint will have a stronger bond with the surface once it fully dries. When the painting is done and the paint fully dry, I finish it off with a clear finish coat to further secure the paint on the shoes and to give it that factory finish look. Custom shoes can be ordered via IG DM at @trippinarts.”

Electrifying talent on these custom design Nike AF1 shoes is visible from the textured neutrals to vibrant colors and attention to detail. The textured neutrals above look like art that you can feel with pronounced variations of dimension and shades, while the squiggled thin lines on the side create even more detail and pattern.

More than enough to draw you in and appreciate the artistry in these individual works of art, Kai also creates detailed designs in bright pops of color like those shown above. The colors contrast in a way that also somehow blends. With this much detail, one can only take a closer look to really see the extent of craftsmanship in this pair of shoes.

Another design features this pink shade that blends in an ombre effect to a thinner minty blue edge around the shoe. Along with that are details including the lines on top that loop around and continuing on the sides of the shoes. Lettering is also stenciled in on the back sides in a clean, artistic way. While not as vibrant as the shoes above, these are also incredibly detailed with a fun, unique color way.

While shoe designing is taking the lead right now, he tells us, “I still try to find time to work on my canvas painting since that's where I can really get creative and have fun. I consider my style to be a mix of abstract art and street art, so my process for making a canvas painting doesn't necessarily have a step by step process like customizing shoes.

I usually have a broad idea to start off with. Then I add whatever color, texts, and image that comes to my mind at the moment to fill up the canvas and use it as an abstract background. After that, I keep layering the canvas with texture and paint until it's done. Smaller canvas works are available at my website For the bigger canvas painting you can find the painting at my IG and DM me for purchase.”

The artistic elements in these canvas paintings are like none other! As you can see in the Bogey, available on his website and shared on Instagram, a great amount of detail is involved along with vibrant, almost three dimensional accents that seem to jump off the canvas. The dynamic energy can be felt through art while the eyes and skull show a sense of apathy.

The prince crown adds another level of detail to complement the art and bring out further messages in the painting.

What is Kai Sasaki’s mission for his work and designs?

He says that it is to show his artwork to a broader audience and peak their interest in one way or another. The way that he makes his artwork allows for viewers to enjoy and appreciate it in different ways. He tells us that “you can just simply enjoy the painting visually, or you can look at the artwork a little closer and find some messages and images and wonder about the message of the work.”

Finding inspiration in the moment, the drive for a work of art can come from “the song lyrics that were playing at the time, thoughts that were going through my head, and mood I'm in.” He tells us that because feelings are often hard to put into words, that's where he uses abstraction to visually show what he feels by shapes and colors. This is completely evident in his artwork, as you can see the emotion and the train of thought visually as though it is jumping out of the painting and pulling you in to that moment he was in while working on the piece of art.

Giving back to Hawaii and the aina is an important matter to us, so we asked how Kai as an artist is giving back. He tells us, “I eventually want to have a group art show to promote local artists in Hawai’i and their works. With the current situation with COVID it's hard to have a gathering and also socializing so this is probably going to take a while.”

The drive to share other artist work and promote local designers is something we have in common and admire in Kai Sasaki! Supporting and building others up plays an essential role in the creative industry, especially among local artists in Hawaii.

We finish our time with Kai by inquiring about his end goal and how he plans to phase up to a whole new place and take his business to the next level. His response?

“I want to use my shoe customizing as a marketing tool and eventually paint on canvas for full time. I'd like to partner up with a gallery who can showcase my work to the public, and in time I'd love to have my own gallery to show my work and other local artists' works to help them get recognition.”

An honorable ambition, we feel inspired by Kai Sasaki for not only his exceptional talent and works of art but his dedication to local artists and creation of art that brings out the feelings in all who come across his work. Expect to see much more from this artist, as this is only the beginning!

Story written by:

Katlin Tara O'Carroll for KAPA Magazine

Personal Stylist/Fashion Blogger

Photography by: @KaelaTeho

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