A great commissioned painting should feel like it was always meant to hang above your bar, behind your desk, or in that suspiciously under-decorated golf room. Knowing how to commission a painting is less about speaking in art-world code and more about giving a good artist enough direction to make something personal without turning the project into a committee meeting.
The best commissions start with a clear reason for the piece. Maybe you want a cinematic portrait of your dog in a vintage jacket. Maybe your home bar needs a painting with more personality than another neon sign. Maybe you are buying a gift for the person who already owns every decent bottle, club, watch, and gadget. The point is not to have every brushstroke planned. The point is to know what you want the artwork to do when it hits the wall.
Start With the Wall, Not the Painting
Before you pick a subject, look at the room. A commission is not just an image you like on a screen. It is a physical object with a job to do in a space.
Measure the area where it will hang, including the furniture underneath it. A painting over a sofa, credenza, bar cart, or desk usually needs enough scale to hold its own. Tiny art on a big wall can look less "minimal" and more "we forgot to finish the room." On the other hand, a massive statement piece may be exactly right for a media room or a long blank hallway.
Take a few photos of the room in normal daylight and at night with the lamps on. Those photos help an artist understand the existing colors, materials, and overall attitude of the space. A moody whiskey-bar painting can handle deeper tones. A bright office may call for bolder color and cleaner contrast. If the room already has loud wallpaper, patterned rugs, and enough visual noise to qualify as a minor parade, a simpler composition may work better.
Also decide whether this is meant to be the room’s main event or a supporting player. A single original painting can anchor a wall. If it is joining a gallery wall, it needs to cooperate with the surrounding pieces without becoming wallpaper itself.
Choose an Artist for Their Point of View
The fastest way to end up disappointed is to hire an artist whose work you do not genuinely like and ask them to paint in someone else’s style. You are commissioning their eye, not ordering a custom pizza with every topping imaginable.
Study an artist’s existing work. Look for the things they repeatedly do well: expressive faces, dramatic lighting, loose brushwork, tight realism, humor, atmosphere, sports subjects, old-Hollywood swagger, or cinematic storytelling. If their work makes you stop scrolling, you are in the right neighborhood.
Style matters because a reference image is only the starting point. A strong artist will interpret it through their own visual language. That is where the character comes from. You can ask for a James Bond-inspired mood, a Caddyshack-level golf reference, or a portrait that gives your dog the authority of a retired casino owner. But give the artist room to make it art rather than a literal copy of a screenshot.
At Gregory Classics, for example, a commission works best when the client wants original artwork with Madison Gregory’s recognizable painterly energy, not a factory-perfect replica of an image found online. That distinction is worth understanding before money changes hands.
Write a Brief That Gives Direction Without Choking the Life Out of It
You do not need to write a novel. In fact, the best commission briefs are usually clear, specific, and short enough that a real human can use them.
Start with the subject. Say who or what is in the painting and why it matters. A beloved family dog, a favorite golf hole, a movie-inspired scene, a meaningful place, or a larger-than-life portrait all give the artist a foundation.
Then explain the mood. Words like dark, funny, elegant, gritty, nostalgic, colorful, restrained, cinematic, or irreverent are useful because they tell the artist how the piece should feel. Mention where it will live, too. “For a dark walnut home bar with brass fixtures” is far more helpful than “make it cool.”
Reference photos are essential when the commission includes a person, pet, house, boat, or specific location. Send the sharpest photos you have, preferably from a few angles. For portraits, include images with good lighting and visible facial details. A blurry phone photo taken from across a parking lot may capture a fond memory, but it cannot tell an artist what someone’s eyes look like.
If you have inspiration images, label what you like about each one. Maybe it is the warm palette in one photo, the composition in another, and the dramatic shadow in a third. Do not expect an artist to combine 14 unrelated pictures into one coherent painting without a little interpretation. That way lies chaos, and possibly a horse in a tuxedo standing in front of a mountain because nobody clarified anything.
Talk Budget, Size, and Materials Early
Commission pricing varies because paintings are not interchangeable products. Size, medium, number of figures, background detail, framing, shipping, and an artist’s demand all affect the final number.
Be direct about your budget from the start. A good artist can tell you what is possible at that level, whether that means adjusting the dimensions, simplifying the background, choosing a different medium, or moving from an original to a museum-quality fine art print. There is no prize for pretending the budget is unlimited until the estimate arrives.
Original oil paintings typically require more time and carry a higher price than a print or a quick study. That is part of the appeal: you are buying a one-of-one object with actual layers of paint, texture, and the artist’s hand in it. But it depends on what matters most to you. If you want a meaningful piece in several sizes or need multiple gifts, a hand-signed archival print may be the smarter play.
Ask whether the quoted price includes shipping, framing, sales tax, and revisions. Clarify the final dimensions in inches, including whether the piece will be framed. A 24-by-36-inch canvas feels very different on a wall than a 16-by-20, even if both sounded substantial while you were sitting at the kitchen table.
Agree on the Process Before Work Begins
A professional commission should have a simple written agreement or clear order details. It does not need to read like a corporate merger, but it should cover the basics: subject, size, medium, price, deposit, timeline, revision policy, shipping, and what happens if the project changes significantly.
Most artists ask for a deposit before beginning. That protects their time and confirms that the project is real. It is normal. So is a timeline that accounts for drying time, other work in progress, framing, and shipping. Original oil paintings especially cannot be rushed simply because a birthday appeared on the calendar six weeks ago.
Ask how approvals work. Some artists share a sketch or composition before painting begins. Others work more independently and provide progress updates at key stages. Neither approach is automatically better. If you need to approve the layout before color goes down, say so early. If you chose the artist because you trust their instincts, resist the urge to direct every square inch from your phone.
Revisions deserve a grown-up conversation. Small adjustments may be part of the process, particularly at the sketch stage. Major changes after the painting is nearly complete may cost more or may not be practical. Changing “a black Labrador in a bar” to “a black Labrador on a sailboat in Monaco” is not a minor note.
Know the Difference Between Inspiration and Copying
Commissioning a painting based on a beloved film, athlete, musician, or fictional character can be a blast. It can also involve intellectual-property considerations, especially when the work is intended for commercial use, public display, or reproduction. A private, one-of-one commission is a different situation from ordering artwork that will be sold, printed, or used in advertising.
Be honest about your intended use. If the piece is for your own home, say that. If it is for a business, product packaging, social media campaign, or promotional event, the artist needs to know before quoting the project. Usage rights and ownership of the physical painting are not always the same thing.
The same goes for reference photography. You may own a photo on your phone, but a professional photo taken by someone else can carry its own rights. When in doubt, use your own photos, obtain permission, or ask the artist what they need.
Give the Finished Painting a Proper Landing Spot
When the painting arrives, do not lean it against a wall for six months while you “figure out framing.” Get it up. Originals deserve proper handling, sensible lighting, and enough breathing room to be seen.
Avoid direct, harsh sun and hang the work away from damp areas, heat vents, and the splash zone near a bathroom sink. Use appropriate hardware for the piece’s weight. If it is framed under glass, keep lighting angles in mind so your guests see the art instead of a perfect reflection of themselves holding a drink.
The best commission is not the one with the most instructions. It is the one where your story, your space, and an artist’s point of view meet in the middle. Give the artist a sharp brief, a realistic budget, and enough creative oxygen, then make room on the wall for something nobody else owns.