Lela Harris, Wilfrid Wood and Sarah Moulden on judging portraits

Lela Harris, Wilfrid Wood and Sarah Moulden judged the Portrait category for the 2026 Koestler Awards this year.

Lela is a self-taught artist whose portraits, built from archival research and imagination, give voice to people overlooked by history. Wilfrid is a London-based sculptor and portrait artist known for drawing and modelling his subjects from life. Sarah is Senior Curator of Nineteenth-Century Collections at the National Portrait Gallery.

While here, they shared their thoughts on what makes a good portrait, and advice for anyone thinking of entering the Koestler Awards for the first time.

Our conversation was edited for brevity and clarity.

Thank you all for being here today. To kick off: what makes for a good portrait? What makes for a bad one? Or is there such a thing?

Lela: A bad portrait is something that doesn’t make you feel anything about it. A good portrait is one that you either love, or hate, or feel something in between, but you have a reaction to it.

Sarah: Something that speaks to you. A good portrait can stop you in your tracks.

Wilfrid: I think it’s really nice when you get a feeling of the character of the person coming through the portrait.

Wilfrid, you’ve mentioned before that so much good portraiture has already been made. How do you shake that feeling of “it’s all been done before” and make it your own?

Wilfrid: The greatest portraits may already have been painted; hundreds of thousands of incredible portraits exist, and what on earth could an artist now add to that? But you’re living in a different world, and there are always new people, new faces, new characters, channeled through the artist. So there’s always going to be something relevant to say about the contemporary world.

Sarah: And arguably every portrait is as individual as the sitter. You have, in a sense, infinite subjects. We’re always speaking, writing and painting out of our own time, so it’s always relevant. And it’s also about how you engage with the portraiture of the past, riffing on it… The past can tell us so much about the present.

Lela: I also think a lot of people are overlooked, in terms of the archive and the historical portrait narrative. The “greats” tend to be portraits of people deemed important by other people deemed important, and plenty of people are excluded from that. So even though there are mind-blowing, incredible portraits already in the world, there are still so many stories to be discovered in the archives, or reimagined.

What’s the best advice or criticism you ever got about your art? What did you value most?

Sarah: “Sarah, don’t paint, write about it instead.”

Lela: That is harsh! I think mine was “Don’t take art, take business studies, because you’ll never get a job unless you do business.”

Sarah: Was that the worst? Or best?

Lela: Honestly, both. I only really became an artist in the last six years, past 40. I’m a late starter, but art can start at any time. And the business studies did actually help, because being an artist also means doing a load of boring admin, and business studies helps with that.

Wilfrid: I started oil painting about three years ago, and I know a guy in my studio who’s like a proper oil painter, and he’s been oil painting all his life. And I said to him, “I’m finding this very difficult, oil painting’s quite difficult, isn’t it?” And he said, “No, it isn’t.”

That’s the best bit of advice I’ve ever had, because it freed me! I mean, it’s as difficult as you make it.

What would you say to someone who hesitates to call themselves an artist, even if they’re making art day to day?

Wilfrid: Someone once told me that if you keep going, drawing, painting, sculpture, whatever it is, you’ll find your own voice. You can’t help but. It just happens. But it takes a lot of dedication. If you can dedicate yourself and keep going on and on and on, something will emerge. You can relax and think: “Something will emerge.”

Lela: I agree wholeheartedly. Over the last six years, I kept worrying at the beginning that I didn’t have a style. And then when I stopped worrying about having a style, I was like: “Oh, I think I found my style!”

So it’s important to just keep making, make as much as you can. Pick one thing out of a piece of work that you’ve made, even if you hate that piece. It could be an eyebrow, an eyelash, a quirk in how you did the eyes. Take that one thing into your next piece and build on it. You can only make (as we like to say in our house) good art when you’ve made bad art. So you have to embrace the bad to get to the good.

Sarah: I wonder whether some of that is a privilege that comes with getting older: feeling freer, enjoying yourself more. Joy is a big part of this. If you’re not enjoying what you’re doing, you need to find a way to enjoy it, or change to something you do, because life’s too short.

A lot of artists seem to fear getting it wrong or not being able to justify why they’re drawn to a particular medium or piece over another. Where do you think that comes from?

Wilfrid: Going back to what Sarah was saying, it’s a great thing about getting older: you just stop caring as much. I blast through with my opinions, however daft they are. I’ll say “I really love this one” for very little reason, and I can’t be bothered to justify it. I’m not at all intellectual! My reaction to work is all gut instinct. I don’t care if people think I’m stupid or shallow.

Sarah: I love that. There’s a fear of saying the right or wrong thing: a binary way of thinking about art, which is really about creativity, but also about commerce, reputation and the idea of genius, all of which go back hundreds of years.

I work in a big museum, and we’re always trying to work out how to break down barriers so people feel able to come in, enjoy themselves and have opinions, all of which are valid. It doesn’t really matter what you feel about a piece. Whether you think it’s good or bad, or don’t fully know what you think. It’s all valid.

Lela: I agree wholeheartedly. I’ve come at this sideways: I’ve got no formal art training, so I’m not really sure what “the rules” are, and I don’t pay much attention to them. I just respond to work with my gut. It’s liberating, actually.

Today we all had different opinions but found common ground. That kind of open conversation doesn’t happen enough, not just in the art world but more broadly.

A lot of the work we see is of pop culture icons, celebrities, imagined figures. Do you think portraiture works just as well from the imagination? Do you need someone there in front of you?

Sarah: A portrait isn’t only the sitter and the artist, it’s also the viewer, bringing their own preconceptions, understanding and imagination to the work. But if you don’t have a model or a sitter, that doesn’t make something not a portrait. It’s about resurfacing or reimagining, breathing life into a figure and giving that figure a story.

Lela: What I enjoy most in my work is combining archival research with imagination to centre someone history has overlooked. You can use archival photography from a similar period as a skeleton for what someone might have looked like, then use imagination, or “fabulation,” as the writer and academic Saidiya Hartman calls it, to put yourself in that person’s shoes. To think of them not as a burial or baptism record, but as somebody’s brother, sister, auntie or friend, and try to imagine what their life was like.

For artists working within restrictions, in prison, for example, there’s still a lot of scope: research through a library if available, imagination, memory. You can draw yourself (even if you’re your own harshest critic!) or draw the people around you, if you can carry a sketchbook.

Wilfrid: I don’t have very much imagination, honestly. I’m hooked on drawing and painting things that are right in front of me, which is what I do nearly all the time. I couldn’t begin to do what you do, Lela, it seems extraordinary.

What advice would you give to entrants who are thinking of entering portraits? We’ve got 52 other categories entrants could choose: music, mosaics, hairstyling and barbering, fashion. Out of all of that, why portraiture?

Lela: If you want to be an artist, hobbyist or professional, you have to be brave. Sharing your work with other people is the hardest part, but also the best part, because it’s how you connect. There’s no right or wrong way to make art. If you’re proud of a piece, submit it. We’d love to see it.

Sarah: On choosing portraiture: it’s about human connection, about people, about relationships that matter. Portraiture gives you that immediately. Just submit it and go for it!

Wilfrid: If the three of us as judges are anything to go by, we’ve all got very different tastes, so most people would be in with a chance. There isn’t a “house style” we’re after.

Lela: I’ll also say, having been on the receiving end of both rejection and acceptance as an artist: it’s really tough when your work doesn’t get in. But that’s usually not down to the artwork itself, it’s down to the restrictions of judging on the day. If you don’t get in this time, there’s a good chance you’ll get in next time.

Keep going!

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