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7 Steps to Commissioning Your Perfect Portrait

Have you ever been gift shopping for that one friend or relative who has everything? Have countless hours of shopping for something unique left you frustrated and disheartened? Why not try a fine art portrait? Portraits are just about the most personalized gift you can give! Presenting your loved one with a painting or drawing of themselves shows that you truly want to make their day special. Wondering where to start? Look no further! Let the following 7 steps be your ultimate portrait gift-giving guide.

"Camille and her Girls" copyright Shelly Denning 2017

Step 1: Choose your image

The majority of modern artists prefer (or at a minimum, have the ability) to work from photographs. Gone are the days of sitting for several hours every day while the artist painstakingly paints your portrait in your study. Painting from photos allows you the freedom to go about your day and gives the artist the ability to work at his own pace. Not to mention that this is absolutely essential if your portrait is to be given as a surprise.

When searching for the perfect photograph, it's best to find one that is well lit and shows the subject's personality. While a pretty smile straight into the camera is fine, you might find that candid shots typically translate better to the canvas and will illicit a stronger emotion. If you don't currently have any photos that seem fitting, look over the person's Facebook page or contact friends or family members and inform them of your intentions. Chances are, you'll end up with more options than you expected. If you're really lucky, you may even find someone who is interested in splitting the cost with you.

It is important that your image be sent to the artist at the highest resolution possible. Facebook is notorious for lowering image quality once uploaded. This doesn't mean you can't use a photo you've downloaded, but have a few back-up options, just in case. If you're scanning a photo yourself, be sure to scan at the highest quality available on your scanner. When submitting the photos to the artist, send your favorite three, if possible. It's best to upload them to a file sharing service such as Google Docs or Dropbox. This allows you to get large files to the artist easily and also eliminates any trepidation he might have of downloading attachments for fear of possible viruses. While this is a good general rule, before sending anything, you should also ask your artist if he has his own guidelines for submitting photos.

Step 2: Pick your medium

The medium you choose can affect your artwork greatly. For instance, if your brother's birthday is in a week, an oil painting is not going to work for you because oil can take up to two years to fully dry. Medium is also a stylistic choice. While I've seen acrylic paintings that look like oil paintings, it's highly unlikely that a pencil drawing is going to look like a watercolor painting. If you're unfamiliar with the look of the various media available, a quick internet search will remedy that in a flash. Below, I've outlined some of the more common mediums and provided a few details on each. Don't overlook non-traditional mediums as well for a truly unique art experience. I've seen portraits made with everything from discarded gum to bingo daubers.

Examples of some of my work in different mediums.


This is a fairly simple medium that can result in some fun nuances. You can't always predict what this medium will do, often giving the artist some "happy little accidents" a la Bob Ross. Watercolor usually results in a very fluid and translucent painting. It is difficult to get photo-realism in watercolor.

Time: fast

Surfaces: paper

Finishing: sprayed with a sealant, framing behind glass and with a mat recommended


Pencil is great for getting lots of detail and depth in a grayscale drawing. With pencil, you can do anything from light sketching to deep photo-realistic drawings.

Time: fast to extensive

Surfaces: paper, wood

Finishing: sprayed with a sealant, framing behind glass and with a mat recommended


Similar to pencil, but with a few distinct differences. Obviously, being in color is the main difference. Also, depending on the type of colored pencil, you can get anything from a sketchy drawing to photo-realism to a more painterly quality.

Time: moderate

Surfaces: paper, wood

Finishing: sprayed with a sealant, framing behind glass and with a mat recommended


This is a great medium if you want something more stylized. Because of the fast drying time, acrylic is difficult to blend and therefore difficult to achieve photo-realism. Acrylic is great for pop-art styles and more choppy paintings. It's also great if you're looking for something more opaque with a heavier feel than watercolor.

Time: moderate

Surfaces: canvas, paper, wood, glass, plastic, fabric

Finishing: not required, but occasionally varnished; framing (without glass) optional


Oil is the most versatile and perhaps the most classic medium. It can be used to achieve any number of styles from chunky to hyper-realistic. Because oil takes some time to dry, it is not ideal for projects requiring a quick turnaround. However, this same slow drying time allows the artist to blend effortlessly and to take their time to create a flawless product.

Time: extensive

Surfaces: canvas, paper, wood, glass, plastic

Finishing: not required, but occasionally varnished; framing (without glass) optional


These mediums are similar and are often used together. Charcoal is typically black, but other colors are available. If something other than grayscale is desired, pastels may be used to colorize it without changing the style. These are very loose and messy tools and usually result in a piece containing minimal detail. The images are typically more implied with light and shadow resulting in a very sketchy look.

Time: moderate

Surfaces: paper, wood

Finishing: sprayed with a sealant, framing behind glass and with a mat recommended


Oil pastels may be used alone to create a low-detail look similar to chalk and charcoal (but smoother) or graphite (pencil) may be added to increase the depth and detail. Oil pastels take a little longer to dry, allowing manipulation over a period of time.

Time: extensive

Surface: paper

Finishing: sprayed with a sealant, framing behind glass and with a mat recommended


While typically associated with more cartoonish or comic book art, many artists have learned to manipulate these mediums in a way that no one ever could have anticipated. Modern art markers are made to be blended and layered, but require skill to utilize them well. Pen and ink are similar in that the artist must be confident in their abilities. There's no erasing ink.

Time: fast

Surfaces: paper, wood

Finishing: not required, but occasionally sprayed with a sealant; framing behind glass and with a mat recommended


Airbrush has been around for a while as a tool for hobbyists, only being accepted into the fine art world in the past few decades. This is more of a delivery tool (much like a paint brush) than an actual medium as various media may be thinned down and applied by airbrush. Used alone, this tool can be used to create beautifully-blended, soft images. Used in conjunction with ink, acrylic or other media, hyper-realism can be achieved.

Time: depends on the medium used

Surfaces: depends on the medium used

Finishing: depends on the medium used

Various styles that I do.

Step 3: What style do you prefer?

Styles are as unique as the artists themselves. New ways of expressing art appear almost daily. This is perhaps the most difficult question of them all. What message do you hope to send with your portrait? Are you drawn to paintings that look like photographs or do you prefer a looser, more interpretive style? Think about your recipient as well. If he is older and more traditional in his taste, perhaps a direct representation of the photo would be the best option. A younger, edgier friend may delight in a colorful, geometric design. Your medium may determine some of the stylistic choices, but the possibilities truly are endless.

Examples of how different sizes may look.

Step 4: Choose the size

Regardless of medium, the price of your commissioned piece will generally increase exponentially with the size. You probably will not make a final decision on size until after getting some pricing from your artist, but you should at least have a ball-park idea of what you want. Think about the recipient of your gift. In what kind of place does she live? A small apartment may not lend itself to a large painting, but a small drawing may look lost in a mansion. Does she tend to move often? If so, the extra effort required to pack a large painting, may be more than she cares to handle. Does she live far away? You still have to get the gift to her and a larger piece will cost more to ship. When thinking of size, don't forget to take into account the additional space taken up by mats and frames, should you choose to include these.

Step 5: When do you need it?

This is a simple question, but definitely an important factor to discuss with your artist. If she is highly sought after or in the middle of a show, she may not have time to make your deadline. When making your initial contact, the date should most definitely be mentioned. It would be a shame to spend three days working out the details of the painting only to find that the artist won't be able to complete it until next year when you need it next week.

Step 6: Determining your budget

Many a budding artist will be happy to accept $20 to do a lopsided 10 minute sketch of your grandmother. If you're not turned off by the fact that it may look like Golem, spend away! I'm not saying that all beginning artists are unskilled, but most decent artists are going to request a rate that matches the quality of their work. Some artists have pricing listed on their website, but don't hesitate to contact someone whose work you admire, even if you can't find any pricing available. Let your artist know what kind of price range you have in mind and they'll let you know what they can do for you.

Step 7: Finding your artist

In the modern age, finding a portrait artist has been made relatively easy. Simply typing “portrait artist” into your favorite search engine will undoubtedly provide you with more possibilities than you realized. Finding good portrait artists may prove a bit more challenging. Numerous online galleries exist with even more artist-run websites. The sheer volume of it can be overwhelming.

Rather than visit sites directly and taking the time to sort through artist after artist, I recommend a different approach. Once you've determined the medium and style you want, build a search around this. Example search parameters may be “photo-realistic oil portrait artist” or “pop-art acrylic portrait artist”. If you'd like to work with someone local, add your city to your search field.

Hit enter and then select the option for images. Scroll through until you find some examples that appeal to you. By clicking on the image and maybe doing a little digging, you can usually find out who painted/drew the piece. Any artist who is currently working should have a website, Facebook page or Instagram profile that is easily found by searching for their name and typing “art” or “artist” behind it. If you can't find them, move on to the next. However, if your search yields positive results, explore his site. Does he list an option for pricing? Take a look at the options to determine whether he's in your price range. If pricing is not available, send him a message outlining your needs (using this article as a guide) and request a quote.

I recommend contacting at least five artists (I hope I'm one of them!) to give you several options from which to choose. Perhaps one doesn't take commissions, but can point you in the right direction. Maybe another doesn't respond at all. The majority of artists are happy to take the work and will compete for your business. Using this technique, I'm certain that you'll find the perfect artist to match your perfect gift.

Purchasing a portrait can be a scary thing, but the results should be fun and exciting. Armed with your new-found arsenal of information, you're well on your way to becoming known as the friend who always gives the perfect gift. You also have my permission to be a little selfish and get a portrait of yourself, as well. Go ahead. You deserve it for being such an awesome friend!

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