An Artist to Know: Caroline Chriss

I’ve been friends with Caroline Chriss for years on instagram and have watched her grow as an artist and entrepreneur. Her work is beachy and fun with relaxed vibe. It’s no surprise that Serena & Lily and Well & Wonder sell her paintings now! She also just launched a sandal and silk scarf line which you will LOVE.

I was beyond honored when she offered to create a custom piece for us. Caroline is known for capturing Nantucket in her artwork and I was thrilled to have her create something special for our family.

Brant Point Lighthouse in Nantucket is a special place to my husband so putting our family there in a painting was perfect.

Me wishing I could jump right in the painting

I thought it would be fun to do a Q&A with Caroline as she has an interesting background. I love her helpful tips and recommendations!

I saw you worked for Oprah’s magazine and Ralph Lauren! How were those experiences?

During my time at Parsons I was lucky enough to intern at Oprah Magazine and Ralph Lauren. After graduating, I began working full time at Ralph Lauren on the Men’s Apparel Showroom team, where we were in charge of designing the showrooms that Ralph would walk through! I really could not of loved this job more. It was the perfect place for me to grow creatively before going off on my own! In fact, I loved it so much I occasionally freelance for the same team now that I back in NYC J

How long did you live in Chicago? What were your favorite places/things to do in Chicago? 

I lived in Chicago for 2.5 years and absolutely loved it!! I resided on Sheffield in Lincoln Park and one of my favorite things to do was to take long walks around LP and look at all beautiful town homes. I would always stop in my favorite stores on Armitage along the way too (Shout out to Art Effect, Loris Shoes, and Serena and Lily!!) I also was a huge fan of Big Star Tacos and Nicks for late night jazz!

Favorite spots in Nantucket?

Sconset has a very special place in heart!! My family has always stayed in Sconset for 2 weeks every summer for the past 25 years, so that is where all my fondest memories are! I think my Happy Place in Nantucket is the Summer House. There is nothing better than grabbing an after dinner cocktail and listening to Jaimie play the piano there. Some of my other favorites are Buck a Shuck at Jetties Sand Bar, Ventuno, Cisco Brewery, and the Nantucket ghost walk!

 Any tips for someone interested in turning a passion into a career?

You can do it… I promise you!!! Make sure you maintain patience, perseverance, and self-belief throughout process.! I learned quite quickly that being a full-time artist was not going to come quickly or easily. I knew I was going to have to put all of my time and energy into it, and be very self-disciplined, if I was going to make it work.  A pivotal point for me in my career path was reading the book “When to Jump” by a friend Mike Lewis. This book made me realize that I needed to stop looking to the outside for permission to pursue my passion, but instead, look to the inside and get that permission from myself. Once I mustered up the courage and gave myself the go ahead, my career as an artist truly began.

What has been your favorite piece that you have created?

Although my favorite paintings change constantly as I keep creating, I always go back to “Summer Sky and Sea”.  It took me a while to define my artistic style but this is one of my first seascapes where it really clicked for me. I will never let it go because of that! It is currently hanging in my living room.

Artwork does NOT have to match your home but I love that this fits in PERFECTLY with the blues and pink.
Here’s a close up. Can you find our family? Three little girlies and us!
I still have to get it framed and even when I do, I’ll be keeping Caroline’s business card and handwritten note in the back.

Caroline offers commissioned pieces and has a beautiful website where you can purchase her prints, originals, scarves and more fun pieces:

Caroline Chriss – website

You can also contact her via email at for more info on commissioned pieces. Thank you Caroline for a piece that we will treasure forever! xx

Samantha Regan

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