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Drawing the hands takes a tremendous amount of practice. After all, if you're going to include hands in your portraits, you want them to be as well thought out as the head. The hands express another facet of your subjects' personality. They add character to a man's portrait, grace and poise to a woman's portrait, and charm to a child's portrait. And if you can't put in the hands, you're forever limited to just head and shoulder portraits - not much fun!  
At the outset I would like to make clear the fact that there is no specific rule or formula for drawing any object and the hand is no exception. However, in view of the complexity of form and movement inherent in hands, it is true that they do present many difficulties to the draughtsman and painter.  
The achievement of fullness, variety and clarity at one at the same time is always a problem and particularly so, it seems, in dealing with the forms of the hands. 
The fact that we are aware of being surrounded more often by clothed individuals than otherwise 
has led to our being almost as conditioned in our attitude to hands as we have become to the 
human face. They have come to be regarded as expressive features of the human being, 
subsidiary only to the face, and our incurious familiarity with them continually comes between us and any endeavor to view them in an objective manner.  
It is then rather on account of their familiarity to us than the reverse that they are deserving if not demanding of separate study. It is my hope that the following drawings, diagrams and text may be of real service and not simply an aid to the accumulation of a series of smart tricks to be applied mechanically.  
When dealing with any of the forms in nature, and by that I mean everything around us, a process of rationalization takes place: We endeavor to reduce an object to simple understandable terms by considering its function and its component parts separately.  
Such an element of analysis is present in every drawing of worth, although in the case of master 
drawings it is not always apparent, occurring, as it does, instinctively and almost at the moment of 
It should be kept in mind that although we shall be observing the nature of hands separately, it is 
important that we continually remind ourselves of the fact that they form a part only of a larger 
unit - the human figure - and are only fully expressive when related to it. 
NOTE; On some of the following drawings you will see some printed text that you will not be able to read. I scanned these images from a workbook that I give to each of my students. Don't be concerned, I will add the text below, above or beside each drawing.
Here and below, I have drawn a series of hands in different positions in what can be called a three-dimensional diagram form. That is to say that only the simplest surfaces or planes have been employed in building up the structure.  
This type of drawing by means of basic solid geometry forms is very valuable in developing a 
feeling for essentials and may be useful as a preliminary probe when you are faced with complexities which might otherwise appear unsolvable.  
Notice the relative absence of curved planes. In simplified constructions as contrasted with finished drawings nearly all the surfaces meet at a definite angle. This is to remind ourselves that everything, no matter what, has a front, back, sides, top, and bottom. 
 Regard the fatty part just below the thumb, as a part of the thumb. (top drawing) 
Observe the end planes of the finger tips in foreshortened positions. (top drawing) Watch the 
position of the joints in relation to one another. (bottom drawing) Think always of the structure 
and never merely of the silhouette. Only in this way will you learn to draw with expressiveness.  
 If in doubt, draw in the triangles even if it destroys a "pretty" drawing. 
Observe the size of the hand in comparison with the size of the head. The most common fault is to make the hands too small. 
The position of the fingernails in relation to the fingertips is a good indication as to whether the finger is foreshortened. "A" (the longest line) is obviously pointing more directly at us than "B". The tip does not show below the nail. 
Always relate your drawing to geometric forms. If need be, practice by placing a geometric form in 
your subjects' hand. By this method, the relationships will be close at hand, so to speak.  
HERE ARE SOME FACTS ABOUT THE HAND AND WRIST: The wrist is a form similar to a flat
block, approximately twice as wide as it is thick. The wrist rotates with the hand on the forearm.
When the hand is at rest, palm up or palm down, in one's lap or on a table, the front of the wrist,
on the thumb side, is higher than the little-finger side. Prove this to yourself by studying your own
wrist and hand.
When the arm lies flat, palm down, on a flat surface, there is always a hollow under the wrist. The
arm and hand never rest on the wrist, but on the heel of the hand and the fleshy part of the
forearm near the elbow.
The hand is made up of two masses: the hand itself and the thumb. There are four bones in the
hand mass, twelve in the fingers, and three in the thumb.
TIP; A common mistake when drawing hands is to make them too big or too small. The length of
the hand from its heel to the tip of the longest finger is considered to be the length of the face,
from chin to hairline.
The hand is so complex a structure and capable of so many movements that most students are
apprehensive about drawing or painting it. However, to the portrait painter, the hand is second in
importance only to the head, adding so much to the character of the work that we absolutely must
give it our best effort.
Let's set aside our fears and attempt to see the hand as a geometric form. If we look at it as a mitten with thickness, we can master it. This is a valid way to block in the hand in any medium - 
charcoal, oils, watercolor - and can be relied on to get you started on the hands in all the portraits you do for the rest of your life.  
This first form is a good beginning, but you'll never see a hand in this position - out flat - on real people, so we must explore further. 
The knuckles (on the back of the hand) are halfway between the wrist and the end of the first finger, the index finger. Check this on your own hand. Let your blocked -in mitten bend at this point so that the "hand' appears more natural, slightly cupped. The middle finger is the longest and it determines the length of the hand.  
The finger section A - B is jointed twice more and can bend forward at these joints all the way to a tight fold, a clenched fist.  
The hand section B - C is capable of movement at the wrist forward and backward and side to side. 
The first section of the finger, starting at the knuckle, is the longest of the three finger parts. The second section, in the middle, is shorter than this, but longer than the third section, the fingertip.  
As none of the fingers are of equal length, none of these divisions line up across the finger mass. 
however, these segments - the longer section from the knuckle to the next longest to the shortest - are still the structure of every finger.  
Each section of each finger is always straight, never curved. Even when you see the most graceful  willowy hand movements, the fingers may curve, but each segment (called a phalange) is straight. 
Draw these finger sections with straight lines on the top side, and with rounded fatty pads on the lower, the palm side. Think of each segment as a cylinder and you will get the prospective right.  
The hand is naturally cupped when in repose. We really have to PUSH to flatten our hands on a flat surface. Cupped from fingernails to heel, the hand is also cupped from side to side. Knowing this will help remind you to round the form across the knuckles in any view. The only time the hand is flat is when a conscious effort is made to extend the fingers. 
The thumb may be considered a long form with squared sides. It has three joints; the base joint is out of sight in the hand and connected to the wrist. 
The fingers and the thumb fan out from the wrist. However, the visible joint where the thumb joins the hand is nowhere near the finger joints and is never in a line with them unless the hand is tightly closed, as when making a fist. The thumb dominates the hand, particularly when the hand is holding on to something. 

Scroll back up and look at the last three illustrations. we have been studying the back of the hand.
Now turn the hand over, palm up as in the illustrations. Looking at the fingers, you can see there
are three parts to each finger - three fleshy pads, all quite equal on any one finger. Of course, since
the fingers are not all the same length, the pads and the folds between them do not line up with
each other across the hand.
You'd think the folds on each finger would match the joint divisions on the back of the finger,
wouldn't you? Study your own hand carefully.
There is the fold at the third joint, the fingertip joint. Then the second section and the first joint.
On the palm side, this is where the fingers end and the palm begins. Now fold your hand at the
knuckles - you are in for a surprise - the fingers do NOT fold at this third joint where they join the
hand; the knuckle joint on the back corresponds with a FOURTH fold across the palm of the
hand! This is where the finger action starts!
Look at your own hand from the side to prove that the third fold on the inside is only halfway
between the second joint and the knuckle joint on the back. Curl your fingers halfway closed and
see this amazing fact for yourself, first from the thumb side, then from the little finger side. There
is no movement where the fingers appear to attach to the hand, but at the knuckles further down in
the hand mass. Knowing this will help you to draw hands in natural positions.
By now you're probably thinking, "how am I going to remember all that"? No one expects you to
remember it! I only hope one day when you're in the middle of a portrait and having trouble with the hands (all of us do, you know), you'll look back at this lesson and find the answer to the problem that's plaguing you. Most often the problem is in the basic construction and not the details. I can't stress this too strongly. I could give you the clearest, sharpest photograph of hands in the world, and you could spend days and weeks painting from it, but without real knowledge of how the hand is constructed and how it works, your painting will be lifeless and without substance.
Remember, artists don't paint only what they see; they paint what they know