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How to Paint a Gift Portrait

Updated on November 9, 2008
Masai Man by Robert A. Sloan
Masai Man by Robert A. Sloan

Painting when you Don't Know How Yet

I'm a serious artist. I've been doing art ever since I was a little kid, when my family looked at my drawings and decided I was the next Picasso. (They didn't get it that I was more interested in being the next Ray Bradbury, maybe with a bit of the next Leonardo da Vinci on the side. I liked realism, invention and science fiction illustration!)

You might have been doing art or decorative art for a while now or you could be reading this because the idea of doing art is something you think you stink at. Maybe this article is the beginner article that'll give you the magic trick to creating recognizable art other people like, so they don't feel like you're just being cheap if you gave them a picture of their kid for the holidays instead of buying something.

Guess what? I've taught art to complete beginners who swore up and down that they had No Talent. Within six months to a year the worst of them was selling their art for actual money. So this is that article. It's put together from all my experiences teaching those classes to help you find a short cut to do a picture that your family members and dear friends will think is awesome.

The trick is to cheat.

Do not surprise them with this gift. Ask them for permission to use the best photo of their baby or their dog or themselves that you can. You can tell a good picture from a bad one. You know what you like. What you want for this is the one they picked out to have printed 8 x 10" or 11" x 14" -- nice and big for framing on the wall. Because that is easiest to draw from.

Got that? Okay. You're going to need some supplies for this too. Some of these are necessary. Others involve choices. But we're going to keep it very easy and relatively cheap, and remember that if you get it right for one relative, you can get another piece of the fancy paper for another relative and another, the more of these you create the better they will look.

Try a self portrait too while you're at it. Then your first one can be hidden back in your sketchbook if you got some serious problem with it and you can try again till you get it looking better.


Inexpensive frame with a precut mat that comes with it and has a mat opening of 8" x 10" -- the frame should be bigger, get the size that has that size opening. It'll be an impressive picture that way. You can work larger, but it takes having a copier that will print out your reference photo legal size or bigger.

Tracing Paper, get a whole pad of it in case you mess up and need to redo it. Also there are several tracing stages.

6B or 9B graphite pencil -- smudgy like charcoal

Normal HB or No. 2 Pencil

Use of a copier

Cotton buds

Extras that may help: a chamois (get it from an auto store cheaper than an art store), a Kneaded Eraser (any art store), a white vinyl eraser (don't use the pink ones, they streak), some Colour Shapers (something like a rubber paint brush for moving pastel around, use Firm for oil pastel and Soft for soft pastel), a fan brush, a light box like the Artograph Lightracer to make tracing easier, a sketchbook with a lot of pages for practice, charcoal for practice.

If you want to make it a black and white portrait, get gray paper, charcoal and a piece of white charcoal or black and white charcoal pencils. This is another way to do it for less cost and saves you needing to choose colors at all. It could also look dramatic with a red-brown Conte crayon and a white one on tan or beige paper and still save you needing to choose colors at all. The little four-pack "Matchbox" set of Conte crayons has Dark Brown, two Sanguine lighter and darker and White. This is perfect for the Easy Monochrome Approach.

Soft pastels (powdery kind) preferably good ones, Skin Tones or Portrait assortment (Loew-Cornell are artist grade good ones! Alphacolor is not, and professional artists laugh at it. Ask the art store counter clerk or Blick's customer service which ones are Artist Grade or at least Student. Artist Grade work better.)OR

Color Conte crayons, Portrait set of 12 or Assorted 24 or 48 (these are VERY high quality and not as expensive as some of the artist grade soft pastels), Sanford NuPastel, Polychromos pastel sticks, Derwent color sticks, the type of pastels that are harder sticks but still powdery smudgy blend with your fingers. I recommend the Conte from personal experience and because the big set is reasonably priced for a big set and has lots of skin tones. Those tiny sticks do last a good long time and the colors mix better than most of the rest.

Sennelier oil pastels or Caran d'Ache Neopastel or Holbein Artists oil pastel or Erengi Art Aspirer oil pastel. Don't get the cheap ones even if the price is tempting. They will fade fast, within a year or so, and you'll be stuck with the same family member complaining to you about it because you'll still be related next year.

Colored pastel paper such as Canson Mi-Tientes "Moonstone" or tan or beige, a middle color that's a little pinkish or brownish. Not green or gray. Canson Mi-Tientes makes some inexpensive Scrapbooker pads of pastel paper in Heritage (dark colors), Neutrals (the one you want) and Brights. Pick up that Neutrals pad for practice even if you're going to go fancier with either of these optional sheet at a time super expensive artist papers. They DO make pastel art easier:

Hahnemuhle Velour Paper, available at Blick and probably at some of the stores like Michaels. THIS is a great cheat. Anything you do on it is going to look wonderful. It's expensive at $5 a sheet but boy does it get a super effect for less work. The trick to using Artist Grade materials is that you often get more bang for your buck. They literally make it easier. OR

Colourfix sanded pastel paper, again in a medium color not too light or dark, that leans toward pink or brown. You can make some yourself if you buy watercolor paper -- must be 140lb, the heavy kind, can be the super heavy 300lb -- and a pint of Colourfix Pastel Primer. Clear will let you tint the paper with thinned acrylic or watercolor to exactly what you want, but for this you may want to choose a color that's medium value (how light or dark it is) and warm colored. (warm colors are yellow, red, orange, pink and brown, cold colors are green, blue, purple and gray). A watercolor pad and a pint of primer will let you try again and again for a lot cheaper. Use foam brushes to apply the primer to the paper and just use it in the outline of the picture area.

We are going to trace the photo carefully according to some steps, then color it. If you can color something and stay within the lines, you can do this portrait. That is why you are going to get great art when you don't know how. If you do it this way often enough, you will start taking short cuts and drawing small details instead of tracing them.

We chose pastel so that you can't do that many small details anyway and it comes out well on the first go. Pastel can be easily reworked if you got it wrong. Go outside the lines and you can color over the wrong bit and bring the line back.

Make a black and white copy of your reference photo. Either use the best photo you took or get permission to use theirs, to avoid copyright infringement. Now put the tracing paper over the photo. If your photo was little, take it to a copier stand and blow it up till it's big enough for a portrait. Keep in mind that you want to fit the head inside a standard size mat opening like 8" x 10" or 11" x 14" so make the copy a good size. Given that copiers do letter size, let's try for an 8" x 10" portrait.

Be sure your good paper is bigger, like 9" x 12" or letter size, so there is some border to go under the mat. Weirdly, sometimes using a bad photo for a reference can work better because you don't get distracted by all the fine details.

Make sure the photo has good lighting though -- strong light from one side. Make the person whose portrait you want to do sit to the side of a sunny window or a strong lamp. The problem with most snapshots is the flash. So use your phone camera or digital camera without flash, then enlarge and enlarge and enlarge the printout. If they got a photographer to do a portrait, half your work is done for you from their good lighting and professional composition. Glamour Shots can be flattering.

But so are pastel portraits since they are soft and you can't draw in every wrinkle.

Now that you have all the stuff together, I'll show you what kind of tracings to do with line drawings in pen. Do yours in pencil or charcoal pencil. They can be erased.

Outline of the head and a little shoulders to where the edge of the picture will be. Use this to place the head on the page.
Outline of the head and a little shoulders to where the edge of the picture will be. Use this to place the head on the page.

If you have a light box, tape the copy to the top and tape the tracing paper over it. If not, tape the copy to a sunny window during the day and tape the tracing paper over it.

Trace it exactly the size it is. Do the outline of the whole head including the hair. Carefully remove that tracing and set it aside. You got a whole pad of tracing paper, right? If you mess it up, do a new one. My example is a freehand sketch because I'm used to doing those. But you're a beginner -- trace carefully.

This is what we're going to use to place the head on the good paper -- velour paper or sanded paper or colored pastel paper like Ingres or Fabriano or Canson mi-TIentes. That stuff costs a lot, so we are going to try it on the sketchbook first.

This will get you good looking results, but it's not easy. If you really are bad at drawing, plan to spend a lot of time in these early stages before you can trace accurately and copy and shade what you traced well enough to use the good supplies and do it. Consider doing a bunch of charcoal ones in your sketchbook.

If you use the kind of sketchbook like the Canson Universal Recycled that has microperforations and do your practice ones in charcoal, that's the best. That way if your practice portrait looks better than your final one, you can remove it on the perforations and use that for your gift instead of the messed up one.

We are being real here. Art takes practice even with all the help and aids you can get, like tracing. But the good thing is that practice has some dramatic effects. If you go through this process with more than one person or the same person a dozen times, you'll get to where doing the next present takes doing it only once and it'll take a lot less time getting it right.

Eventually, if you do lots of portraits, you'll get to where tracing is too cumbersome. You'll know where things are and try drawing freehand. There are good books on drawing freehand that can help. The main thing is that if you do a good tracing of every detail on the face and compare it to a beginner freehand drawing, say a self portrait you sketch in charcoal, you will see that in the tracing all the features are the right size for the face and placed correctly in relation to each other.

Most beginners don't bother putting in the forehead. Or place the head so high on the page it cuts off right above the eyebrows, which is no good for a formal portrait even if it looks good in the sketchbook. Common errors are making the eyes too large, or one eye bigger than the other, the mouth too large or small, the nose funny shaped even if it's accurate or just a weird shape, leave out the ears, put the ears too high, get too much hair on the sides and not much up top, not have room for eyebrows.

These common facial proportion distortions are instinct. We all did them before we learned the real proportions of human faces. They emphasize the emotional features -- eyes and mouth, and skip or reduce the boring forehead. Three things on a face are dark and obvious by contrast -- eyelashes defining eye shape, the line between the lips, and eyebrows.

Those move and waggle and express emotion. They are also symbolic. Everyone can tell what feeling a smiley shows unless they have certain learning disabilities that blank out the ability to read facial expression. So these key features move, change shape constantly and are not as easy to draw as a ball or a cone or a block. Photos get them the right size in relation to each other.

There are a couple of ways besides tracing to get the proportions right. One is grid method -- draw a grid of squares on your copy of the photo, and draw the same grid very lightly on your paper. Then copy exactly what's in each little square carefully, light and dark.

If you can use Grid Method, it is slow and accurate. Doing a charcoal portrait by Grid Method and then carefully erasing the grid lines with your kneaded eraser will make an accurate portrait.

Another, the one I learned with and reinvented, is Tick Marks. I put grid coordinates across the top and right side of my picture area and my photo reference, then measured from the top and one side to where a dark spot meets light, like the corner of one eye. I made a tick mark at the same measured place on my art paper -- a very small dot put on the shadow side of where it belonged.

I did both sides of the eye, a dot for top and bottom of the eye, both corners of the mouth, dots for top and bottom of lips, dots to the lowest part of chin, dots going around the chin, the first one I did was a connect-the-dots picture with several hundred dots. But it came out accurate and I did not need to erase a grid. I used fewer Tick Marks every time after that, as I got used to the proportions of the face.

If you practice repeatedly with the same photo, you will eventually learn that person's proportions. We are going to trace, so that you can get this done faster, but the principle is the same. If I had the sense to trace first I might have finished sooner and done more of them and learned faster.

So let's do the next tracing.

Contour drawing of Masai Man. Notice my mistakes, corrected. I've been doing this for years and still make mistakes. Yours are no big deal either.
Contour drawing of Masai Man. Notice my mistakes, corrected. I've been doing this for years and still make mistakes. Yours are no big deal either.

The second tracing you make will be a contour drawing that shows the darkest areas within the face. Because I didn't take my time doing the sketch and used ink, I made a pretty major mistake on my first drawing to demonstrate what outlines to trace. I placed his ear way too high.

So I corrected the line without removing the old line. You can practice in your sketchbook doing this and it's fine, but since you're new to it, try to do a fresh tracing that has the right lines instead of what I just demonstrated. Do as I say, not as I do. Seriously, the more careful you are at this stage, the better results you will have.

This contour drawing is a type of sketch most professional artists use. It just establishes where everything is by drawing the darkest spaces. If you have a light colored subject -- say a white haired pale skinned person -- against a dark background, then drawing the outline of the background will define where the person is.

But there will still be shadows on the face that define the shapes of the face. Most of these are not black and white. I'm going to ink in the very dark darks of my contour drawing here so that you see what that does.

If you do this in pencil and then ink it, just doing the very darkest darks and no middle shades, this creates a very graphic looking artwork that is dramatic in itself and if accurate, will give the likeness. I outlined a couple of the next darkest areas too, so I will use a black pen and a gray pen for coloring my contour drawing.

Contour drawing with deepest darks filled in black, medium dark filled in gray.
Contour drawing with deepest darks filled in black, medium dark filled in gray.

This is a contour drawing filled in with the deepest darks in black, and the medium-darks in gray. I followed the shapes of the areas as well as I could, given the distortions of my first mistake. The dip in his forehead between his eyebrow and cheekbone is placed too high just as the ear was. So his features are distorted, but the result is still a human being.

I would start this over if it was anything but a simple demonstration sketch, and I did want to show the difference that one proportion error makes. If I had actually traced my Masai Man photo reference or even my finished good portrait, I would not have these errors.

This demo does show how the face breaks up into very dark, medium dark and highlight areas. If you do this on colored paper, you can then look at the photo for where the brightest highlights are and add them with white. Then you have a good likeness.

Black, dark, medium, light and white is enough values in soft pastel or Conte to get a likeness well.

I'm going to show you my real sketch for Masai Man next, so that you can see what the right proportions are.

Tips to successful tracing are: do not move the tracing paper or your copied photo till you have everything traced in perfectly. Go slow and concentrate on keeping your line right on the edge of the light and dark areas. If you mess it up, take a deep breath, stretch, get mad and crumple it and toss it in the trash and start over.

Making mistakes and starting over is the most important part of learning to draw. This isn't an easy project, but you will save money over having to buy a gift that has this kind of value. The one picture anyone likes best is a good picture of someone they love.

My original sketch for Masai Man
My original sketch for Masai Man

Compare this one with today's bad sketch and with the finished portrait. You can see that when I began to color him in, I corrected minor inaccuracies in the sketch. I hinted at where the darks were and then went into them with more than one dark pastel.

Once you have a contour sketch of your portrait that actually fits the photo again when you take it off and put it back, transfer it to a sheet of the Canson paper in medium tan or beige.

To transfer a tracing, turn it over. Turn your pad of Canson mi-Tientes over so that the cardboard on the back is a drawing board too. Now draw a very thick line over the lines with the super soft 6B or 9B pencil. Yep. You're turning it into a transfer sketch.

If it was a vase or something else symmetrical, you could just turn over the tracing to copy it. But faces are not symmetrical, and turning it over may change the likeness till it doesn't look like the person. You can try it, but you're better off doing a thick layer of soft graphite on the back of the lines instead.

You will rub off a reverse of the tracing on whatever cardboard you used for doing this, especially if you don't move the tracing while you go over the lines.

Sharpen your regular pencil to a good point.

Measure the outlines of your picture area on Canson paper (if you got velour or sanded pastel paper for this project, try it on Canson or Fabriano etc. first) by taking the mat board out of the frame, putting that on the paper, center it in a page (unless you got a big sheet, then just leave the opening starting an inch or two in from the side and top) and lightly draw inside the opening with your pencil.

This will give you a rectangle precisely the size of your art. Lighten that by squishing the kneaded eraser on it, so that it doesn't show when you use it to line up the art inside the mat and tape it in. This is your picture area.

Position the traced contour sketch over that rectangle, right side around the way you traced it. Tape it down firmly using low tack artist tape that can be removed without damaging the paper. Working on a hard surface like a table, slowly draw along the lines again carefully. The wider lines of the transfer layer will be lighter than your original lines. Stick to your original lines. Sharpen your pencil as needed.

Be sure to get all the lines. One way to do this is to use a red ball point pen to do the transfer, so that you have red lines where they were transferred and pencil lines where they weren't. Press reasonably hard. Test it on a scrap -- you don't want to press so hard you make an indentation in the paper that will be hard to fill with pastels or oil pastels.

Now move your practice piece on Canson paper onto your drawing board, when the sketch is transferred.

Start coloring with your pastels. Do the first layer by blocking in all the darkest areas. Match the colors in the photo, or get the person to come sit in front of you so that you have truer color matching than the photo. Color is not as important as value though, if you use earth tones (browns and light peach) and more or less match their complexion you'll get it good enough.

Set out your pastels or soft pastels in a range from dark to light. Work from dark to light. With pastels and oil pastels you can put light over dark, so if you go too far in an area, fix it by putting the right color over it.

Look carefully at the real color of the shadows. It may be a little purplish in the deepest darks. Pick the sticks that come closest in value to that area on the face and just color it in like a paint by number. You can even go slower and contour three or four levels of light and dark before getting to highlights.

Always put a little white catchlight dot next to the pupil of the eye. This detail makes the eyes sparkle and look alive. Eyes are wet shiny surfaces and skin is a soft not-shiny matte surface. So the bright highlight on the eye is pure white against pure black and becomes the focal point of the portrait. I put that catchlight in whether it's there or not, but it's there in most photos.

Work around a little bare patch on the iris of the eye touching the pupil to do the catchlight right, so that it's white on bare paper rather than white onto black shading it to gray. If you didn't, roll your kneaded eraser till it's got a point and clean out a little patch before putting the catchlight in.

White highlights on the rest of the face should be softened and blended in. If you're doing charcoal and white, that's good enough. If you're using color, use a light peach instead of pure white for the lightest face highlights. They are usually on the nose, maybe the cheekbone, part of the forehead.

Look closely at the photo for color and shading.

A good trick for coloring accurately or drawing accurately is to turn both the photo and your drawing upside down. Then copy lights, darks and color as accurately as you can.

Within the face, most of your shading will need soft edges. Blur the shading together except where the photo shows a sharp line meeting light and dark. All the shading on the nose is going to be soft shading except maybe the shadow under it that defines its shape -- and unlike my contour drawing that is usually not dark black. The shadow under the chin is going to be another one that may have a hard edge -- a clean sharp edge. The edge between the person and the background will have a sharp edge -- unless it's their hair.

It can be very flattering to do hair loosely and let it go off scribbly or blur a little against the background. Hair does not need to be drawn one hair at a time, that doesn't look as real as doing masses of color that are the right shape with a few highlights drawn in where they show on the photo. On Masai Man, he has short little rolled dreads, so I just did a highlight along each little roll. That was enough to imply the texture of his hair and shade the roll so that it looks three dimensional.

Hair goes in clumps so always use highlight strokes that go in the direction of the hair and float in the middle of the clump, darker at the edges. This goes for anyone's hair. Black hair may have blue or bluish highlights and that's very dramatic.

Get looser and lighter as you get to clothing and hair edges. The most detail should be in the eyes -- the shape of the eyelids and exact colors of everything in the eye area is about a quarter of the time I spend on any portrait. Do the whole face colored in fairly solid, but put more layers of detail into the eyes and mouth than anything else. This takes advantage of that same emotional punch that makes freehand sketchers distort the shape.

Get the shape of the shadows on the nose right and get the value of the shadows on the nose right in relation to each other and the nose will look real. Absolutely do not outline the nose, that is the start of potato-ness.

If you are not sure which colors are the right values, take a strip of paper and draw little blocks of your pastels next to each other, darkest to lightest. Then move that strip up and down on your photo reference till you find the closest match. Value is more important than color. To get the right value in the right color, make a swatch of the right color and start darkening it with the darkest brown or black or purple, or lightening it with white or light colors. Try different mixes till you get it right.

Accurate coloring per area takes a little attention but can be very satisfying and relaxing like any other craft. Blur the edges of color areas together with a fan brush or chamois except where you have those few hard edges. The edges of lips are usually distinct, but not as dark as a drawn outline with a pencil. So define those with color -- match color and then draw a clean line and shade within the lips.

The upper lip shape is always darker and distinct as one shape. The lower lip has a highlight on it and a shadow under it that helps define its shape. Get those shapes and values right to have soft, real looking lips.

Do not, do NOT mess with doing a portrait of someone who is smiling with their teeth showing until you have a lot of practice doing portraits. Teeth are tough! Make it easy on yourself!

The exact pose I used for Masai Man is the most flattering pose for your subject -- 3/4 view with strong light coming on the short side of the face. If you are taking the photo yourself, pose the person next to a bright window or a bright lamp that's up and to the side. Turn their head slightly toward the window. Don't let them smile with their mouth open, tell them to keep it closed and look at you.

Then don't use flash. Flash photography flattens out the face so everyone looks dead. This is why drivers license photos look so bad on everyone. Full forward with a flash is ugly. So don't use that photo unless it is the only one you have and the person is dead. Try to get a 3/4 view.

Practice your portrait first in charcoal and white or dark red and white on gray or beige paper, then do it in color on the Canson type paper. Then once you have done it well on that, trace again and do it on the fancy surface. Velour paper is gorgeous stuff. It's fuzzy. It lets you blend the shading so easily that you will finish in half the time and it'll look twice as good.

Sanded pastel paper is going to rub your fingers raw if you use fingers for blending on it, so use the chamois or fan brush if you're using the sanded paper. Its advantage is that it holds lots of layers for mixing and blending exact colors. If you blend, don't blend the last layers. Pastels are more luminous unblended, and with practice you can blend by going over it with the sticks rather than rubbing it smooth. But you're a beginner -- so blending is a good easy way to get a smooth gradual shading that looks more realistic.

Use your judgement. From that point, start getting creative. Then when you have done it several times, put the best one into the frame and gift wrap it for your loved ones.

If you are giving them paintings of your children, you can do the same photo over and over and get more practice, then give versions of the same portrait to both sets of in laws and any aunts and uncles. Even babies look good in 3/4 view. Be sure to do babies in soft ways, detail only the eyes, light side face shape line and mouth with hard edges.

You can also try this with pet portraits. Be sure to use the catchlight and with animals, to carefully trace all light and dark markings like the stripes on a tabby cat or the yellowish eyebrow patches on a German shepherd. Getting the general shape and markings right is important on an animal portrait, also be sure to use short strokes that always go in the direction of the fur when coloring in. Get the colors right and blended in smooth, then do short distinct highlight strokes just one value lighter than the area to show fur texture.

I hope these instructions help you get started on drawing portraits and enjoying art. Something wonderful happens when you begin to draw the human face accurately. You will discover that every Beautiful Person, handsome actor or gorgeous actress, is funny looking with a weird nose or asymmetrical eyes or weird lips. But everyone will start to look beautiful. You will see people's faces differently after you draw a dozen portraits.

You may get better at recognizing people even when they change their hair style or shave a beard. You will start enjoying people more as you see them as more good looking. The human face is something that we are wired to like down in our bones and blood, and when you learn to draw portraits you'll become a little more of a people person. Creating this gift will actually leave you loving your loved ones more when you finish and get it right.

Once this is learned, you can't forget how to see. It's a change that comes from learning art that stays with you and enriches the rest of your life.

Most of all, even if it takes a lot of tries and practice, enjoy it! When you get it right you will wow people with the ability to make a portrait come to life right before their eyes. It's magic, and you will become the magician who knows how the trick is done.


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    • profile image

      Sierra Mackenzie 

      8 years ago

      Great hub filled with lots of information. I am going to try it.

    • robertsloan2 profile imageAUTHOR


      10 years ago from San Francisco, CA

      Thanks! So glad you like it.

    • vitaeb profile image


      10 years ago from Shenandoah Valley, Virginia

      Wow! Very instructive. My wife is a world class artist. I watch her work and am full of wonderment over you artists! Thanks for this hub!


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