I find that if you can simplify down an illustration to shapes, you end up with a much more clean look with better curves and edges rather than using strictly the pen tool. This isn’t always the case, but for this tutorial it will be, as we use simple shapes and effect to create a retro looking character.
Lets open up a 600x600px document in Adobe Illustrator and make a circle in the middle of the document using the Ellipse tool. Change the stroke to black and the background color to white for now.
To get the shape of our head we are going to go to Effect>Warp>Inflate. Change the Bend to -10% and the Vertical Distortion to 10%.
Since this is an effect still, we want to change it to a line and point, so go to Object>Expand Appearance.
We are going to give our guy a chin, so using the Ellipse tool, draw an oval. Select both the head and the chin, make sure your Pathfinder palette is open (Window>Pathfinder) and click on Add to Shape Area, then expand.
Next we can start working on the eyes. Make a circle by holding down the Shift. We are going to make an eyebrow that will go on top of the eye. To make the eyebrow, draw a rectangle with the Rectangular tool. Draw another shorter rectangle, and line the two ends together similar to what I have done below. You can adjust the angle of the eyebrow to give the character slightly different looks.
Fill the eyebrow and eye with black. Now we are going to add some reflections to the eye by making two overlapping white circles.
Duplicate the eye with Ctrl+C, Ctrl+F, then select everything but the reflection and go to Object>Transform>Reflect.
We are going to start working on the mustache. Start out by making a rectangle and filling it with black.
Go to Effect>Warp>Arc. Change the vertical distortion to 7%. Now go to Object>Expand Appearance.
To add the stylized whiskers at the bottom of the mustache we are going to draw a small box, while holding shift. Hold Shift and rotate the box 45 degrees so it makes a diamond shape.
Click and drag the diamond into the brush palette (Windows>Brushes) and select New Pattern Brush. All of the settings should be good, so just select OK.
Click and drag a line about the size of the mustache, then click on our brush we just made. You can adjust the size of the diamonds by adjusting the stroke size. Put the stroke on the bottom of the mustache and make the edges of the two shapes line up. Go to Object>Expand Appearance.
Select the two parts of the mustache and click on Add to Shape Area in the pathfinder palette. Now we want to draw an oval that will be our mouth. Make the color of the oval white, and the stroke black. Select the oval and the mustache, then go to the Align palette and select Horizontal Align Center.
We also want to draw a nose, so we are going to duplicate the mouth with Ctrl+C, Ctrl+F. Move the circle up, hold down Alt and bring the sides in a little to make the oval a little bit more circular. Change the stroke to none and move the circle above the mustache with Ctrl+Shift+].
We want to line everything up within the head, so first select the mustache, nose and mouth and group them together (Ctrl+G). Select the eyes and eyebrows and group them together also. Select the eyes and head and select Horizontal Align Center in the Align palette. You can adjust the distance between the mustache and the eyes to get different looks
To do the hair we are first going to start by drawing a circle behind his head using the Ellipse tool. Fill the circle in with black and make sure the head has the black stroke and filled with white.
Duplicate the head with Ctrl+C, Ctrl+F. Click on the head and hair, then in the Pathfinder palette click on Subtract from shape area, and then expand. Click on the Direct Selection tool (A) and then the Pen tool (P) (This will let us alternate between the two tools) and then while holding down Alt, click on the top middle point of the hair. Using the arrows move the point to the right, so it is almost above the eye. Also move this point so it is just above the top of the head. Do the same with the bottom middle point. Make sure that point is just below the edge of the head.
Now we want to add a point on each side of the top middle point. Move the points so you have something like what I have below.
On the left side of the hair we want to add a point on the bottom side. Using Alt click and drag the point out and turn it so you have a wavy look.
We are going to add some dark circles around the eyes so ungroup the eyes/eyebrows by going to Object>Ungroup. Duplicate the eye and using Ctrl and Shift make it slightly bigger, so that the new circle goes right to the outer edge of the eyebrow. Drop the opacity down to 20% and the blend mode to Multiply.
Do this with both eyes.
We are going to add a few finishing touches to the face. First I am going to thin out the face a little bit by selecting the head and hair, then while holding Alt, bring the edges in a little. I’m also going to shrink down the eyes a little bit.
Next I am going to add a little color to the face with #FEDEB3. When you fill the color in you’ll notice that the nose is still white. We are going to ungroup the mustache by going to Object>Ungroup, an then click on the mustache and nose, and then go to Subtract from shape area from the Pathfinder palette. Click on expand.
Next we are going to change the color of the mouth to #890C08, with a stroke size of 5pt. Change the stroke of the head to 10pt.
We are also going to change all the black strokes and fills to #2C232B.
We are going to add some ears. To do this use the Ellipse tool and make an oval on one side of the head. Duplicate the ear with Ctrl+C, Ctrl+F and move it to the other side. Make sure the stroke is 10pt.
We are going to start working on the banner, but first we want to select the whole image and go to Object>Path>Outline Stroke. Select the face again and go to Object>Group.
We’ll start off by typing out our product name, with a few spaces in between. Bring our face in and put it in between the two works. Make sure there is enough room for the head to comfortably go above and below the text. Using the Rectangular tool, make a box around it with a black stroke for now.
We are going to add our secondary text below the box, centering each line of text between the edge of the head and the edge of the box.
Duplicate the box and shrink it down to the left side of the box. Move the new box down and in once, while holding Shift. Go to View>Smart Guides, and then click on the new box. Using the Pen tool click on the middle of the new box and while holding Shift, move the point in once.
Duplicate the new box and go to Object>Transform>Reflect and move it to the other side.
To connect the boxes select the Pen tool and make a triangle like I have below.
Select the text boxes and go to Type>Create Outlines. We are going to fill the banner with #890C08 for top part and the back parts are going to be #5C0805.
Also change the main text to white.
Click on the banner and change the stroke color to #2C232B, and the stroke size to 3pt. Click on the three red banner shapes and go to Object>Path>Offset Path and change it to -2px. Change the stroke color to white and stroke to 2pt. Change the stroke of the back parts of the banner to #CCCCCC.
Change the secondary text to #2C232B.
Select everything in the image except the face and go to Effect>Warp>Flag Change the bend to -10%.