Commission a Portrait: What You Need to Know Before Hiring an Artist

When you commission a portrait, a personalized artwork created specifically for you or someone else, often capturing likeness, mood, or meaning beyond a photo. Also known as a custom portrait, it’s not just a painting—it’s a lasting piece of personal history. Unlike a photograph, a portrait painted by hand carries intention, style, and emotion. People do this to honor loved ones, mark milestones, or simply own something no one else has.

Behind every great portrait artist, a professional who specializes in capturing human likeness through traditional or digital media is a process. It starts with a conversation—not just about what the person looks like, but how they want to feel in the final piece. Do you want it formal? Casual? Dramatic? Quiet? The artist needs to know if this is for a wedding, a memorial, a business profile, or just because you love the way someone smiles. That’s why commissioned portrait, a custom artwork ordered directly from an artist based on client specifications isn’t something you order off a website like a T-shirt. It’s a collaboration.

Most artists don’t work from a single photo. They ask for multiple angles, lighting examples, and even videos to study movement and expression. Some want to meet the subject in person. Others work remotely but still need clear references. You’ll also need to talk about size, medium (oil, watercolor, digital), timeline, and budget. A small watercolor portrait might start at $300. A large oil painting with detailed background? That can run $2,000 or more. And yes, it takes weeks—even months—to get it right. No artist worth their salt will rush it.

You’ll also want to see their past work—not just the best pieces, but the full range. Are they good with skin tones? Do their eyes look real? Do they capture personality, or just features? Check reviews. Ask for references. And don’t be afraid to ask: "Have you painted someone who looks like this before?" If they say yes, ask to see it. If they hesitate, that’s a red flag.

And here’s something most people don’t realize: you’re not just buying a painting. You’re buying time, skill, and emotional labor. A good portrait artist doesn’t just copy what they see—they interpret it. They decide where to soften edges, where to add shadow, what to leave out. That’s why two artists painting the same person can create two completely different, equally powerful results.

There’s no magic formula for choosing the right artist. But if you know what you want—not just in looks, but in feeling—you’ll find someone who can deliver. And when you do, you won’t just have a portrait. You’ll have a piece of art that tells a story no camera ever could.

Below, you’ll find real insights from artists, collectors, and experts who’ve walked this path—covering everything from how to talk to an artist, what to expect in the contract, and why some portraits take longer than others. Whether you’re thinking about commissioning your first portrait or just curious how the process works, these posts give you the straight talk you won’t find on a glossy website.