About
I'm Caleb Simmons, a live wedding portrait illustrator based outside Canterbury, Kent, working across London and the South East. I've worked as an illustrator for over 15 years, drawing for clients including Wellcome Trust, Channel 4 and Barclays, and hold an MA in Illustration and a BA in Fine Art.
At weddings, I draw your guests by hand as the day unfolds. Each portrait is finished on the spot and slipped into an envelope for them to take home — a small, personal keepsake made in the room where it all happened. I work quietly and calmly, fitting around your photographer and timings, and the priority is always likeness and memory over novelty.
I'm drawn to weddings that feel personal and considered: houses and barns in Kent, townhouses and hotels in London, places with character. If you'd like quiet live portraits on your day, I'd be glad to hear about your plans.
See more of my work at calebsimmons.co.uk
Why live portraiture clicked for me
For a long time, most of my illustration work happened behind a screen – useful, well‑crafted artwork for studios and clients. It paid the bills, but it didn’t always touch the part of me that fell in love with drawing in the first place: faces, gesture, and the feeling of a particular room at a particular moment.
When I started drawing live – first caricatures outside Canterbury Cathedral, then at events and weddings – something shifted. At one early event I began tucked in a corner, head down, quietly working through a queue. Later in the evening I took my board for a walk through the crowd, and by the end of the night people were half‑jokingly competing for a turn. The real magic wasn’t just the person being drawn; it was their friends watching them appear on paper, recognising them in a few lines.
I realised I didn’t just want to send files off into the ether. I wanted to be in the room, drawing people in real time, with all the warmth and unpredictability that brings.
The work behind
the line
Wedding portraits are one strand of a wider illustration practice.
I’m trained in Fine Art and Illustration, and my work includes theatre posters and visual content as a long‑standing collaborator with Half A String, illustration and animation for companies like Aca Theatre, and book projects such as Wandering Lamb (with Tom Delahunt), which explores neurodiversity and dyslexia in the education system. I also run drawing and “anti‑colouring‑in” workshops that invite people into a more playful, attentive way of seeing.
All of that has sharpened my eye for composition, movement and atmosphere. When I’m at your wedding, you’re not just getting someone who can “do a quick sketch”; you’re getting the same level of craft that goes into building visuals for stages, books and brands – focused entirely on your guests.
More About Me
My wife is a clown — genuinely
I love mountains and wild places; recently carried my one-year old up Snowdon.
I live in a little village in Kent with my family.
Tell me about your day.
I always love the chance to be involved in a couples day and a small part of what makes it memorable. If you feel that live portraiture is right for you please click below.
Even if some details are still being confirmed, that’s ok!
I read every enquiry personally and reply myself, usually within a working day.
Based in Canterbury. Available across London, Kent, and the South East.