Today we’d like to introduce you to Anna Ayres.
Anna, let’s start with your story. We’d love to hear how you got started and how the journey has been so far.
I grew up in Vermont where I played outside all four seasons of the year. A zest for art nurtured by this play in the natural world matured into a finer passion for painting. While attending the University of Vermont studying Studio Art and English, I was introduced to acrylic painting on canvas. After graduating, I traveled often, always returning home to VT with a fresh perspective and desire to put the emotional qualities I felt in our natural world onto canvas. This desire led me to explore beyond acrylic, into both watercolor and mostly oil. I began hanging shows of my original work while attending markets with prints and cards once I had a significant body of work. Five years ago I fulfilled a life long dream to live somewhere warm and close to the water by moving to St Petersburg, FL. Two years ago, I started traveling back to Vermont to attend summer markets there with Anna Hats, one of a kind, handmade hats featuring my artwork. In Florida, I also work for two non-profit organizations in the arts for underserved communities: Nomad Art Bus and Creative Clay Cultural Arts Center. I received an Emerging Artist Grant this summer through Creative Pinellas and am currently working on a new body of original oil work for the final show on September 12th. In December, I will be a part of ArtJones, a 20-artist open studio tour in Gulfport, FL.
Overall, has it been relatively smooth? If not, what were some of the struggles along the way?
Life gives us lemons for a reason. It’s the only way we learn and grow and so any expectation of smooth went out the window when I realized that this little passion of mine wasn’t ever going to burn out. When I first moved to Florida, I sold all my art off before leaving Vermont. At that point, I thought I was done “trying” to be an artist and was going to enter the nursing school once I got settled into Florida. I yearned for stability, something my creative path wasn’t offering me, at least not in the traditional sense. That turned into a yoga teacher certification instead, and I found my way back to painting not long after. The way I think about it now is that stepping into who we truly are is not easy. If it was easy or simple, everyone would be doing it. Realizing our purpose while we’re here is a life-long commitment. When we learn to commit to ourselves over and over, our confidence grows. We learn to love ourselves and value our lives more fully. As artists, this is a key ingredient in making substantial art. Sometimes, I wonder if the best artists of history are simply those who were truest to themselves. Those who carried little doubt and total faith. When I look at it this way, that this life that is essentially choosing me, is a life-long commitment of learning how to put what’s on the inside, out, then the road bumps don’t feel so much like “struggles” but more like necessary cogs in the wheel to reveal the next great thing!
Please tell us about Anna Hats & Art by Anna Ayres – what should we know?
I love to paint the natural world, evoking emotional quality through light and shape. I paint everything from large florals to seascapes to pet portraits. My paintings suggest a deeper connection to mother earth, and to the balanced, peaceful life we can lead with that connection.
I began making Anna Hats two years ago, one of a kind hand-painted trucker hats of heart and home. Anna Hats include imagery that encourages an active lifestyle, love for all things natural and positive vibes. I paint anything from mountain ranges to puppy dogs onto hats. One of my favorites was a tropical foliage background with the word “Suenos” (Spanish for dreams) written in white Santa Cruz style lettering. Anna Hats are wearable pieces of art that show the world what makes your heart unique.
Any shoutouts? Who else deserves credit in this story – who has played a meaningful role?
All of my friends and family deserve credit. When you do what you love, eventually everyone gets on board, even if they were non-believers at one time. I consider anyone who has shown support through an art purchase or through words of encouragement, a friend. And it is my goal to return this support by making the best art I can and encouraging everyone I come across to follow their creative urges. It’s one of those really big important things in life that fills us up and helps us feel purposeful and satisfied. I am constantly amazed by my growing community of individuals who continue to show support in small and big ways. I am blessed to have an amazing mentor right now through the Creative Pinellas grant. Carrie Jadus is a St Petersburg oil painting icon. She offers me a wealth of perspective and guidance each time we meet. Connecting with Carrie is really encouraging me to dive deeper and commit to myself more fully as an artist.
Pricing:
- Anna Hats – Hand Painted starting at $95
- Anna Hats – Patch Hats $38
Contact Info:
- Website: iloveannahats.com
- Phone: (802) 598-8082
- Email: artbyannaayres@gmail.com
- Instagram: @iloveannahats
- Facebook: Art by Anna Ayres

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