Not just a likeness, but a presence: How to commission the perfect portrait

Forget name and fame. Choosing a portraitist by reputation alone is the quickest way to make an expensive mistake, because no amount of renown can make up for a mismatch between the painter’s style and the patron’s taste. ‘There’s no point commissioning an artist who paints with very wild and vibrant colours when you’re quiet and sober and don’t want your pictures jumping off the walls,’ says portraitist Nicky Philipps.

Confident sitters know this and trust their instincts: ‘I was starting out, 28 years ago, and one of the wealthiest girls in the world came to my stand at my first-ever art fair,’ says Sara Stewart, the founder of Fine Art Commissions, an agency that connects sitters and painters. ‘She commissioned a young artist I had just taken on — it was £500 for a full length. She could have paid £20,000, but she chose that artist because she liked his style and that should be what it is all about.’

Even before finding the right painter, however, the very first step to a commission is figuring out why to do it and what a portrait actually entails. ‘There are wrong reasons,’ cautions Stewart, ‘principally, when someone is given a portrait as a present and doesn’t actually want it.’ In those cases, what invariably seems to happen is that the sitter doesn’t enjoy sitting, the artist faces an uphill struggle and the picture ends up in an attic. It is also important for prospective sitters to understand from the outset that a painted portrait is very different from a photographic one. ‘As well as being a record of their appearance, it’s the artistic interpretation by whichever painter you choose,’ notes portraitist Isabella Watling.

Indeed, suggests another painter, Jamie Coreth, people should approach a commission as if they were buying a picture from the artist, rather than their specific likeness: ‘They are first and foremost commissioning the painter’s artistic judgement. From my standpoint, it is important to be given the freedom to pursue ideas and to follow creative instinct. The best ideas can be missed if the brief is too controlling. Give the artist time and space to do their thing, with vision and excitement. I know from experience that, if I am happy with a painting, it’s often a result which the sitter will be happy about, too, and I am happiest with works where I have been able to realise an original vision for it.’

Portraiture, believes artist Isabel Douglas-Hamilton, is a collaborative process: ‘It gives me permission to study the sitters and really get to know them, and allows me to make 1,000 different decisions about who they are. I don’t want to capture a definitive version of that person, I want to capture their presence.’ Assuming they are happy with all this, sitters should plan their commission as far ahead as possible: ‘Artists have pipelines, so you might have to wait a year,’ says Douglas-Hamilton — and this is without considering the time it will take to paint the picture or the fact that the final varnish happens some 12 months after the painting is completed. ‘If you have, say, a big birthday at the end of 2027, now would be the time to think about commissioning,’ recommends Philipps.

What happens next, however, slightly differs, depending on whether this is a private or a corporate portrait. Livery companies or universities will usually want any new picture to fit in with their existing collection, so this will to an extent dictate a sitter’s choice of artist, medium and portrait size. Private commissions have more latitude, which is at once thrilling and potentially paralysing. Size is perhaps the easiest to determine: ‘My portraits are always life size, so the sitter has to decide between a head and shoulders, a three-quarters or a full length,’ says Watling.

Guiding factors in picking what to go for are budget, wall space and the amount of detail you would like to include. ‘With head and shoulders, you can’t have a backdrop,’ explains Philipps. ‘There’s nothing worse than people putting a painting or something on the wall behind their head. It interferes with the person and the character. If it’s a full-length picture, that’s a different story. I painted somebody in America sitting at his desk with the object that made his career: false hips, you know, the titanium thing that goes into a leg.’

The choice of medium and artist can often be linked, although many portraitists are equally happy to produce a painting or a drawing. There are advantages to both media, according to Stewart: a painting has great wall presence; a drawing is timeless and generally quicker.

Identifying the right portraitist, on the other hand, is often what first-time sitters find most challenging. As Stewart pointed out with her wealthy-patron example, sitters should pick a painter to whose style they respond naturally, much as they would if buying curtains or furniture. The problem is that art is often wrapped up in an intellectual mystique that tends to make people anxious and leads them to question their own opinion. ‘My job, first and foremost, is to make sitters feel relaxed and trust their own judgement,’ Stewart explains.

Knowing what kind of artworks patrons already have and love and what their houses look like is a great starting point, but she also has another ace up her sleeve: rather than asking people what they like from a portfolio of paintings, she asks them to point out what they don’t. ‘That’s the most revealing and the most helpful. You can get a better idea of what style they would be happy to live with than if you ask them what they enjoy.’ This kind of preliminary research makes all the difference: Philipps recommends looking at a wide range of artist portfolios and narrowing them down into a shortlist.

However, finding the right painter isn’t only a matter of identifying the style that best suits the sitter’s taste. Personal rapport is what turns a good commission into a great one. ‘[People] need to be furnished with all the idiosyncrasies, availability, price, everything of that artist, so that there are no unwelcome surprises,’ believes Philipps.

Coreth recalls as one of his favourite commissions a portrait that required several trips to paint his sitter at home: ‘We spent a lot of time together and became great friends as a result. The better we got to know each other, the clearer I felt about how to paint the portrait in a way that resonated as true to the individual.’ This is why, notes Stewart, ‘you have to work out the chemistry — whether the sitter will get on with the artist. Being an agent is a little like being a creative psychologist.’ For example, conversation is rather like Marmite for artists — some love it, some hate it — so Stewart would never pair up a sitter who dreads silence with a portraitist who likes to work quietly.

Philipps falls into the talking camp, because she finds that it helps dispel nerves: ‘I like to chat to sitters as much as possible, particularly at the beginning, because that creates the dynamic, the vibrancy of the sitting.’ Her secret to breaking the ice is to share ‘some unbelievably ludicrous stories about art’, such as, she laughs, when, at one important art show, a sculptor presented a head positioned on a plank: ‘It was so heavy that the men who took it past the judges had to bring it in two bits; the head came in first, followed by the stand with its little peg — and the judges rejected the head and took the plank.’ This helps sitters relax, which in turn opens the door to a better portrait. ‘Most people are stiff and nervous. They don’t know what they’re in for and they’re terrified of their image being in the hands of some stranger, so the best thing you can do is to chat, have a fun, jokey time, and then they will sink into themselves. They will tilt their head one way or the other and then you’ll find a more interesting pose.’

What if they don’t stop chatting? ‘Then, you just ask them to be quiet when you’re painting their mouth,’ as, indeed, Philipps once did with Elizabeth II.

These days, laments Stewart, there has been an increase in people asking for portraits from existing photographs. In her view, that kind of commission is very hard to do well, as the artist needs to be able to compose the sitter under the correct light: ‘I recommend people to choose artists that paint from life if they have time and want the full “sitting” experience, but the key thing is that they should have at least one sitting from life.’ Indeed, Philipps asks even members of the Royal Family for a sitting, preferably more.

Sometimes, people are hesitant to be painted from life because they are very self-conscious. This happens more frequently with women than men, particularly older ones, for whom, says Philipps, it is often sufficient to ‘put in front of them a glass of whisky, ask them to talk about themselves and they’re away’.

The more bashful sitters should not fear, however, as portraitists are adept at making people feel at ease. ‘One thing that is very useful is to find something they’re good at,’ believes Philipps. ‘I had one girl who sat; she said she had come from her cello practice and I said “Oh my gosh, so clever! I would so love to do that!” and I could visibly see her coming at me at a different level. Those little human touches — they really help.’

Other prospective sitters are concerned about the toll that being painted from life might take on their days. It is true that a commission should allow enough sitting time. ‘I wouldn’t want the portrait to feel performative and I hope getting to know the sitters allows them to be at ease and be themselves,’ says Douglas-Hamilton. ‘I think the worst thing you can do, if you’re commissioning a portrait, is expecting it to be done to a very quick deadline — you might as well just get a photograph, at that point. You want to give the artist time to really get to know you.’

One of her favourite commissions was a portrait of a young man, Victor Hope, who she painted against the backdrop of an elaborate interior. ‘You almost don’t notice the sitter at first — he is completely engrossed in reading and then there’s a dog at his feet, which gives an atmosphere of leisureliness, calmness. It’s like you’re entering into their private world.’ That said, ‘you don’t have to sit for 40 hours for a great portrait,’ reassures Stewart. Every picture is a law unto itself, but, as a rule of thumb, Douglas-Hamilton mentions three to four sittings, each lasting one to two hours, for a small oil head and shoulders. Philipps also tends to do two-hour sittings. She has done longer ones on occasion, but, crucially, a good portraitist can read the room: ‘If people are getting tired or fed up, you just stop the sitting.’ Watling suggests bored sitters ‘listen to something on earphones’.

Thorough preliminary research and a solid relationship with the painter of choice should go a long way towards ensuring patrons will like the resulting portrait. To assuage any residual fears, many artists, such as Douglas-Hamilton, will show people a sketch: ‘What I would do with a commission as big as the Victor Hope one, I would do a small, intimate oil sketch, then show it to the people who’ve commissioned me and say: “This is my idea for the big painting. What do you think?” I’ll never embark on a huge painting without them knowing roughly what my commission or my composition idea is.’

Many artists, even those as experienced as Philipps, are open to feedback from sitters, either directly or, more often, through an agent such as Stewart: ‘I don’t want to have something in the picture that bothers them,’ Philipps explains. ‘That would be awful. I’m not such a diva to think I get it right the whole time.’ If a sitter is being especially sensitive about a facial or body feature, she will endeavour to sort it out. ‘There are various mechanisms you can use to un-highlight something, if necessary. It doesn’t happen very often, but I wouldn’t want to stand there and tell people to get over it, because they wouldn’t. They’d put the painting in the attic and the whole thing would be pointless.’

This article first appeared in the October 14, 2026 issue of Country Life. For more information on how to subscribe, click here.