Black History Month: Conversations in Creativity - Shailan Wynter, Artist
26 October 2026 by Michelle
As part of our Black History Month programme, we're featuring an interview with Shailan Wynter, a Preston-based Portrait Artist.
Shailan Wynter is a Preston-based artist whose work explores music, culture, heritage and identity through portraiture.
His practice centres on acrylics and spray paint, with mixed media, bold colour, layered texture and expressive marks.
Creating since early childhood, Shailan explored drawing, painting and printmaking through school, college and university before developing his current approach. His subjects range from musicians such as Michael Jackson, Usher and Jacquees to historical figures and Windrush pioneers.
His work reflects his mixed Jamaican and English heritage and a personal interest in understanding where he comes from. Through paintings including Caribbean Soul – British Soil, he explores migration, belonging and the connection between Caribbean roots and life in Britain.
Shailan has exhibited at the Harris Museum and Artistry House in Preston. He also led Culture on Canvas, a workshop at the Harris encouraging participants to explore culture, identity and self-expression. He is developing his original paintings and prints alongside commissions.
As part of our Black History Month curated programme this year, we spoke to Shailan about his influences, inspiration and creative process.
“My work brings together the music I love, the people who inspire me and my Jamaican and English heritage. Painting is a way of expressing myself while understanding more about who I am and where I come from. Through bold colour, texture and expressive marks, I explore those connections, giving myself the freedom to experiment and create something personal.”
1. What was your first memory of creativity?
I’ve been making things for as long as I can remember. There’s a photograph of me at about three years old, standing at an easel experimenting with paint and colour, so I’d put the starting point around then.
Growing up, I drew all sorts: animals, mythical beasts, dragons, portraits, landscapes, and imagined utopian and dystopian worlds. Literally anything.
As the years went on, I became more focused on portraiture, but that willingness to experiment has stayed with me.
Even now, I’ll use whatever materials or tools help me create the marks I want.
2. What was your creative journey to get to where you are?
I started making things as a young child and gradually became more interested in portraiture. In high school, I experimented with oil pastels, acrylics, charcoal and graphite. College introduced me to lino cutting, etching and screen printing, then at university I explored palette knives and learned more about art history.
Over time, acrylics and spray paint became the basis of my practice, although I still use mixed media, including Posca pens and whatever helps me create different marks. My work now brings together portraiture, music, culture and heritage, alongside opportunities to exhibit and share my process through workshops.
3. What impact have clients or commissions had on your career?
My commissions have been for local people in Preston, rather than big-name clients. However, some of my musician portraits have received recognition from the people themselves. MC Ren commented with fire emojis on my NWA painting, and DJ Yella reacted to it too. Jacquees’ manager also messaged me saying my painting of him was “fire”. We discussed potentially sending it over, but that didn’t progress. These weren’t commissions or sales to those artists, but they were moments when something I’d created reached the people who inspired it.
4. How do you establish your own style over a period of time, and still stay relevant?
I take inspiration from different artists, including people I discover on social media. You notice elements you connect with and bring those influences together with your own ideas. Over time, that develops into your own creative identity.
I feel I’ve found something recognisable in the colours I use and how I present them on canvas. My paintings can look different, but there’s a relationship between them. I’m flexible, and commissions sometimes take me outside my usual approach, but experimenting has always been part of my practice. I wholeheartedly believe I’m developing a style that feels like my own.
5. Does your process develop thematically, or is it more distinctive and random?
There are definitely themes running through my work, even though the subjects can look quite different.
Music is a big one, and so are culture, identity and heritage. Painting a musician I listen to and painting a Windrush pioneer come from different starting points, but both connect to people and stories that mean something to me. Caribbean Soul – British Soil brings those questions of roots and belonging into a landscape.
I also take on commissions, which can lead me in another direction, but my own work keeps coming back to those interests.
6. What or who has been the biggest creative influence on your work – e.g. the artists, designers or filmmakers you admire and inspire you the most and why?
My biggest creative influence is Chris Brown. It’s the combination of his singing, dancing, painting and fashion: creativity coming through in so many forms.
Michael Jackson is another major influence, whose impact runs through generations of performers I admire.
Closer to home, my mum, Shiryn Wynter, is an artist who paints landscapes and flowers in oils. We went to university together, with her joining the year below me after I inspired her to enrol. Seeing her build a life around her artwork is inspiring.
I also draw ideas from artists on social media rather than one particular established painter.
7. What inspires you or provokes the motivation towards creativity within?
Music, people and my own background give me a lot to work with. Sometimes the starting point is a musician whose work I connect with; other times it’s a story about heritage or history that I want to explore.
Being mixed Jamaican and English has made identity a personal subject for me.
Painting Black figures is connected to that search for understanding and representation. My Windrush work gives me a way to explore the people and stories behind that history, while also thinking about how Caribbean heritage connects with life in Britain.
8. What is it you love most about what you do?
Painting gives me a way to express myself through colour, texture and the subjects I choose. I can bring together different parts of my life, whether that’s music, culture or my own background.
There’s also freedom in being able to explore an idea in my own way.
With Culture on Canvas, I wanted to give other people space to express themselves too, rather than feeling there was one correct way to paint. That idea matters to my own work as well: having room to experiment and make something personal.
Follow Shailan on social media to see what he's up to and support his work.
Instagram: shailans_artwork
Facebook: Shailans_artworks
TikTok: shailans_artwork
About Conversations in Creativity
Creative Lancashire's Conversations in Creativity programme is a publication and series of talks and interventions where practitioners from around the world, and across disciplines, explore how creative inspiration informs process.
Previous contributors include Lubaina Himid, Halima Cassel, Adaesi Ukairo, Jahday Ford, Hemingway Design, Nick Park, Keith Brymer Jones, Patrick Grant, Lemn Sissay, and Jeanette Winterson to name a few.
