• Bridney Casillas

The Art of Winter Dior Madison

Visual Artist Explains The Inspiration Behind Their Art and How It Relates to Their Self-Identity


By Bridney Casillas

Candid photo of Winter Dior Madison photographed by photographer, Hailey Remillard.

Winter Dior Madison is a 28-year-old visual artist from New London, Connecticut. Their art is influenced and inspired by their self-journey as trans, more specifically, transmasculine.


"Being trans influences my art pretty heavily, just as much as being black and filipinx, or being on the autistic spectrum does. I think it’s impossible to separate lived experiences from your art."

Winter believes that an artist's identity and background has a lot to do with what is being depicted in their art. As a non-binary visual artist, Winter urges the public and art lovers to support queer and black artists to show more representation in the art community.


"I wish there was more queer representation within the art world, but I do think that queer artists are on the rise. I think that in the past, straight white men got most of the attention, and they still do of course," says Winter.

Cup of Soup, 2020. Acrylic on Canvas. 18" x 24"

Currently attending art school, Winter says it has been inspiring, although challenging at times. Working at home in a cramped space, they have been receiving classroom instruction via Zoom.


As someone who enjoys school, Winter says it is important to keep art programs alive in the public school system for children because more artists are needed in the community.


Besides focusing on school, Winter has also been working on their art and says their figures are "speaking" for themselves and the messages behind each painting is becoming easier to interpret.


Strictly an acrylic painter, they recently purchased oil sticks and is looking forward to exploring a new medium. The best thing about being an artist for Winter is being able to freely express themselves in a career field that has no rules.

"My style is very vibrant, chaotic, and has no ambitions to be perfect. That represents me as a person... I have always been pretty weird, and maybe at times a little too sure of myself."

According to Winter, their style can be compared to a "somber hug from a friend, or a colorful slap in the face." Some of their pieces can display both senses of style, as their characters continue to evolve.


Their characters have gone through an evolution since the first art piece they created. When they first started painting, they called their characters "creeps," as they originated from the night terrors and sleep paralysis they experienced for most of their life.


Over time, their characters have been depicted with and without horns. Most recently, their characters have gained noses and one arm.


400, 2020. Mixed Media on Canvas. 11" x 14"

Winter's characters represent themselves as well as black and brown people. Describing their work as political, each painting has its own story, touching on the themes of capitalism, gender, race, and disillusionment, to name a few.

Their art falls into the category of neo-expressionism, a style of art that depicts abstract humans emotionally or sentimentally using vibrant colors. Noting the art style as expressive, wild, and chaotic, Winter says it has so much emotion, which the majority of it is also political.


Citing Jean-Michel Basquiat as their favorite artist who falls into the category of neo-expressionism, Winter says they can connect to his work and can relate to him as a person.


"He was such an interesting figure, and he is not just some long-dead old white guy. He was a POC (person of color) artist that shook things up."


Winter enjoys painting their abstract figures, noting that it could be considered a child-like approach to visual expression. Even though art is not always liberating or therapeutic, they refer to it as being hard work, just like any other job, as they often feel pressure within themselves when they paint.


"Sometimes, I am freed by it, and sometimes I feel that I am trying so hard to get it right, to my standards and expectations."

A short, holiday Q&A was conducted with Winter Dior Madison, as they discussed their Christmas favorites.


Bridney C: As the Christmas holiday approaches, what is one festive activity you enjoy doing?

Winter Dior Madison: I am kind of a grinch... Christmas is my least favorite holiday, and I am an atheist, so it doesn’t have a spiritual connotation for me. However, I love a party. I will rarely pass up an opportunity to eat, drink, and be merry.


BC: How do you plan to stay in the Christmas Spirit during this tough year?

WDM: I think that these are dark and uncertain times. Even if you don’t celebrate any holiday around this time, I think that keeping hope alive through the winter is important. I think it’s always been important.


BC: What is your favorite Christmas dish or dessert to eat?

WDM: I have quite the sweet tooth. Give me the cake, candy, and cookies. Give them all to me. (Laughs)

BC: What is your favorite Christmas song?

WDM: I don't mind listening to Last Christmas by Wham!



Starving, 2020. Acrylic on Loose Canvas. Approx 34" x 50"

Be sure to follow Winter Dior on Instagram for updates on

their art @winterdior_.

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