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 Unilever, 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.
How I work at weddings
On your wedding day, my aim is to fit in smoothly and add something that feels calm, considered and human.
I arrive in good time, check in with the venue or coordinator, and set up a small base where finished drawings can be laid out and collected. For most of the reception I’m on my feet rather than in one fixed spot. I move through the room with a clipboard, usually near natural gathering points like the bar, and invite guests for quick portraits. As I draw one person, people watching often ask to be next.
Each portrait takes a few minutes. I start with the overall shape and posture – how someone holds themselves – and then add details. The aim is a flattering likeness, not a comedy cartoon; people should feel good when they see themselves. We can keep things roaming, create more of a seated setup later on, or mix the two. The exact shape is something I’m happy to collaborate on so it sits naturally within your timings and space.
A few things about me
Weddings are personal, so it helps if you know a little about who you’re inviting into the room.
I live in a little village in Kent with my family.
I was homeschooled, and drawing was how I learned to focus.
Weddings are personal, so it helps if you know a little about who you’re inviting into the room.
I live in a Kent village with my wife – a clown and singer‑songwriter – and our two young children. I was homeschooled for part of my childhood, and drawing was how I focused: notes from the front of the book, worlds from the back. I love mountains and wild places, especially Snowdonia and Cornwall; I’ve even climbed Snowdon with my one‑year‑old on my back. Outside of weddings I collaborate with theatre companies, make illustrations for books and brands, and run drawing workshops.
All of that finds its way into the way I draw: attentive, a little playful, grounded in real people and real places.
My wife is a clown — genuinely
I love mountains and wild places; recently climbed Snowdon with my one‑year‑old on my back.
Our Story7. What others say & what to do next
This is the place to include your Spindrift (or other) testimonial – ideally one or two lines about how it felt to have me there and how guests reacted to the portraits.
If you like the idea of your guests being quietly seen and sent home with something made just for them, live portraits might be a good fit for your day.
You can explore more examples in the gallery, or share a few details about your plans via the enquiry form. I’ll read through what you send, confirm availability, and come back to you with options that make sense for your wedding.
Tell me about your day.
I take a limited number of weddings each year. If you think live portraiture might suit your celebration, fill in what you know — some details can still be unconfirmed.
I read every enquiry personally and reply myself, usually within a working day. No obligation, no hard sell — just an honest conversation about whether it feels like the right fit.
Based in Canterbury. Available across London, Kent, and the South East.