About

Caleb Simmons

Live portrait illustrator. MA Illustration · BA Fine Art. Fifteen years working for animation studios, design agencies, publishers, and theatre companies. Now drawing at weddings and events across Kent, London and the South East.

Canterbury-based MA Illustration · BA Fine Art 15+ years in animation studios, design agencies, theatre Weddings, hospitality, private commissions
How he works

In the room, not in a corner.

For fifteen-plus years I've been drawing people in real time — in studios, on set, in rehearsal rooms, at live events. The context has shifted. The instinct has stayed the same: draw people as they actually are, in the moment they're in.

What changed things early on was being told to stop working in the corner and get into the room. By the end of that evening people were half-jokingly fighting over a turn. It wasn't just about the person being drawn. It was the quiet gasp when someone watches the person they love appear in a few lines on paper — watching a likeness build from nothing, in real time, in their hands a few minutes later.

Weddings are where that instinct found its fullest form. There's a physical object at the end of the day that didn't exist at the start of it — made line by line while the rest of the celebration was happening around it.

"A good portrait says to someone: I have really looked at you."
The work

Not caricature. Not strict realism.

My style sits in the territory you'd recognise from an illustration studio — portraits that are clearly of the person, rooted in their actual features, but rendered with a line quality that feels drawn rather than photographic.

I block in the big shapes first: posture, proportion, the space around the person. Likeness is built from context, not just features.

"Likeness matters, but kindness matters more."
"Imperfection is part of the point."
Analogue drawing has a clumsiness that sneaks in more humanity than a technically perfect image sometimes can.
"The drawing is made in the room."
Not sent off — made in front of the person, handed over the same evening.
Other work

Illustration beyond the event.

Alongside live work, I've spent years making things that need to last. A long-standing collaboration with Half a String theatre — posters, visual worlds, set design. A picture book, Lou, created with Tom Delahunty, about neurodiversity and dyslexia in education. Work with animation studios and design agencies who want someone who can think alongside them, not just execute.

The through-line is the same: draw something that feels alive, not just accurate.

If any of this sounds like the right fit for your wedding or event —

The enquiry form takes five minutes. No obligation, no hard sell. I read every message personally.

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