PUT YOUR WORST FACE FORWARD : (

You could start by drawing a smiley, the simplest and most universal way of drawing faces
It's easy to make the usual form of a sad face smiley.
It's simply a reversal of the familiar smiley face.

Lighted smiley faces are sometimes used at the roadside to indicate whether you're driving below or above the speed limit. Very effective. Facial expressions are understood instantly. You can see at a glance if Big Brother is smiling or frowning, however fast you're whizzing by.
You know the accepted wisdom of the smiley world. An internet smiley can be any colour as long as it's yellow. 
I hate to disillusion you, but a sad face smiley to use when you are blue is more effective if it's - well, blue. 
Smileys, super or sober, 3d, animated or plain, are always always round.
...Except when they're another shape to make life more exciting. If you're having a go at making your own sad face emoticon, you could try a tear drop for a glum expression. 
Smileys show they are unhappy with an upside-down smile.
Wait a minute. Try that in the mirror! Pull down the corners of your mouth as far as they can go. You may get a comical 'Oooh-Er!' grimace. You might even look like a smiley. But do you really look sad?
Ahem. In fact the middle of your lower lip goes up when you're really sad. You only look 'down in the mouth'.
Escalate to a full scale crying fit and your upper lip stretches sideways. Your whole face scrunches up towards the middle as if to squeeze out the tears. Only the outer parts of the brows go down.

A gloomy smiley? Hang on a minute. Isn't that a contradiction in terms?
As a matter of fact, I can't think of any occasion when you'd want to use a really sad face smiley or emoticon. Emoticons so often mean "only joking"...
. .
Sad faces of the more realistic kind can work better for other symbols like theatre masks

TIP To add instant despondency to a sad face smiley, simply give an upward twitch to the inner ends of the eyebrows.
Drawing sad faces. Can't face a Smiley? How about a Gloomy...
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