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How to Create a Stylized Captain’s Portrait in Adobe Illustrator

Final product image
What You'll Be Creating

Ahoy, mateys! In this tutorial we will learn how to draw a stylized flat portrait of a funny captain, using basic shapes, warp effects and some custom brushes and textures. Get ready and hoist the sails!

1. Form the Captain’s Head

Step 1

Start by taking the Rounded Rectangle Tool in Adobe Illustrator, click it once on the Artboard to reveal the pop-up menu, and set the Corner Radius to 5 px. Form an even square by holding down the Shift button, and fill it with linear gradient from pale yellow in the bottom to darker pink on top, imitating a skin tone.

make a head base with  Rounded Rectangle Tool

Step 2

Let’s start forming a nose by adding another rounded rectangle and applying a linear gradient from light pink to white. Switch the Blending Mode to Multiply in the Transparency panel, thus darkening the nose and making it blend nicely with the face. Move the nose closer to the left side of the face shape, making the head of our character turned to the side a bit, like the three-quarter view used in portraits.

form a nose with Rounded Rectangle Tool

Step 3

Add another rectangle perpendicular to the nose bridge, and add two tiny dark brown squares for the nostrils.

form the nose and nostrils

Step 4

Now let’s render the tip of the nose! Add another pinkish rectangle and move it closer to the left, partially covering the left nostril. Copy the nose tip and Paste it in Front twice (Control-C > Control-F > Control-F). Move the upper copy up and to the right a bit by pressing the up and right arrow keys a few times. 

Select both the moved shape and the one below it and use the Minus Front function of the Pathfinder panel to cut off the unwanted parts, leaving only a thin stroke. Apply the same gradient in Multiply Blending Mode as we have on the bridge of the nose. For this purpose, just select the created thin stroke, take the Eyedropper Tool (I), and pick the color gradient from the nose bridge, thus forming a gentle shadow on the tip of the nose and making it more prominent.

form a nose tip

Step 5

Time to add some highlights! Put a couple of rectangles above the nose bridge and the nose tip, filling them with linear gradient from brown to black. Switch the Blending Mode to Screen, creating a warm overtone.

add highlights in screen blending mode

Step 6

Let’s add a pair of cartoon eyes and fill them with gradient from grey to white. Add two more rectangles in Multiply Blending Mode behind the eyes to deepen the eye-sockets.

add eyes

We need to fix the overlapping parts of the nose bridge and the shadows around the eyes. For this purpose, select all three shapes and take the Shape Builder Tool (Shift-M). Now you can click and drag the mouse over the parts you want to unite. Let’s unite those parts of the eye shadows which are hidden behind the nose bridge.

unite the shapes with shape builder tool

Step 7

Add a couple of thick eyebrows, filling them with linear gradient from light brown at the upper edge to darker brown at the bottom. Rotate one of the brows a bit, creating a friendly look on the captain’s face.

add eye brows

Step 8

Form a simple ear by making a small rounded rectangle, filled with skin tone color. Select the Eraser Tool (Shift-E), hold down the Alt key, click your left mouse button and drag the mouse over the left part of the ear. You will see a white rectangle covering the shape. Release the mouse button in order to delete the unneeded part. Duplicate the ear shape, reducing the size of the copy slightly and making it darker to form the inner part of the ear. 

Create a bigger rounded rectangle and Send it to Back (Shift-Control-[), behind all other objects. Fill the newly created shape with the same brown gradient as on the eyebrows, forming a thick beard.

form the ear and the beard

Step 9

Let’s continue styling the sailor’s beard by adding another rounded rectangle perpendicular to the basic beard shape. Keeping it selected, go to Object > Path > Add Anchor Points. Select the lower point in the middle of the bottom part of the rectangle with the Direct Selection Tool (A) and Convert selected anchor point to smooth by clicking the Convert button in the control panel above. Finally, drag the modified point down a bit, creating a nice curve.

style the beard

Step 10

Find the spot where the bottom part of the beard intersects the basic beard shape and add another anchor point with the Add Anchor Point Tool (+). Select one of the anchor handles with the Direct Selection Tool (A) and, holding down the Shift key, rotate the handles perpendicular to their initial position. Adjust the length of the anchor handles to make a nice flowing line.

style the beard 2

Step 11

Select both beard parts and Unite them in Pathfinder. Duplicate the beard twice and move the upper copy up and to the right, as we did with the nose tip. Use the Minus Front function to cut off the unwanted parts.

style the beard 3

Fill the created part with the linear gradient from light brown to white, and switch it to Multiply Blending Mode, forming a shadow in the bottom part of the beard.

style the beard 4

Step 12

Let’s make our captain more brutal by styling a bushy moustache! Start by adding a small rounded rectangle on the left part of his face and place it behind the nose (Control-[). Duplicate the created shape and drag the copy down and to the right. Press Control-D once to repeat the last action, creating another copy.

add mustache

Select all three parts of the moustache and use the Reflect Tool (O) to create a mirrored copy, forming the second half of the moustache on the other side of the face. Add a tiny pink rectangle for the lower lip of the character.

add mustache  2

2. Create the Captain’s Hat & Clothes

Step 1

We’ll begin with the character’s forage cap. First of all, let’s form the cap peak. Take the Polygon Tool and set the Sides quantity to 3 in order to make a triangle. Squash the shape and Convert its upper anchor point to smooth. Select the anchor point in the bottom part of the shape and move it up with the up arrow key. Place the cap peak above the captain’s forehead and make it more three-dimensional by adding a gentle highlight in Screen Blending Mode.

render the forage cap

Step 2

Make a narrow rounded rectangle filled with linear gradient from dark blue to lighter blue. Go to Effect > Warp > Arc and set the Horizontal Bend value to 22% to make the shape slightly arched. Object > Expand the shape and place it under the cap peak, thus creating a decorative cap edging.

render the forage cap 2

Step 3

Add a golden button with the help of the Ellipse Tool (L) by placing one even circle inside the other and filling both of them with linear gradient from dark orange to bright yellow. Move on and start forming the top of the cap by making a light greyish-blue rectangle with the Rectangle Tool (M).

render the forage cap 3

Step 4

Transform the shape by moving its upper right anchor point down, making a sharp angle on the upper left side. Create a similar shape to form the second half of the forage hat. Darken the colors of the cap and add a simple anchor emblem to the front part, making the cap more detailed. You can find out how to make a simple anchor silhouette in my Seamless Anchor Pattern in Adobe Illustrator tutorial.

render the forage cap 4

Step 5

Add an upside-down triangle for the chest, filling it with skin tone, and form a neck-piece made up of two triangles. Fill them with linear gradient from dark blue to light blue on top, adding dimension to the shoulders. Put a couple of white stripes on both sides of the neck-piece.

form the clothes

Step 6

Add a wide ellipse to shape the body of our captain, making him broad-shouldered and manly.

shape the body from the ellipse

3. Make a Smoking Pipe & Stylized Smoke

Step 1

Start forming the upper part of the pipe by creating a squashed ellipse and filling it with dark brown linear gradient. Create the inner part of the pipe by placing a smaller, darker squashed ellipse inside the first one.

render the smoking pipe

Step 2

Render the bottom part of the pipe by adding a dark brown rounded rectangle and erasing its upper half with the Eraser Tool (Shift-E) as we did with the captain’s ear. Make a copy of that part and move it to the right in order to create a highlight with the help of the Minus Front function of Pathfinder and Screen Blending Mode.

render the smoking pipe 2

Move the highlight from the edge closer to the center and make a couple of strokes with the Eraser Tool (Shift-E), crossing the highlight.

render the smoking pipe 3

Step 3

Form the mouthpiece of our pipe by making a narrow rounded rectangle. Go to Effect > Warp > Arc and set the Vertical Bend value to 8%, making the rectangle much wider from the left side. Object > Expand Appearance of the shape and apply the Arc effect once again, but this time set the Horizontal Bend value to 57% to make the shape smooth and arched. Don’t forget to Expand the object in order to apply the effect completely.  

Form the mouthpiece of our pipe

Step 4

Place the mouthpiece between the captain’s moustache and his lower lip and combine both parts of the smoking pipe, adding a golden overtone to make the pipe look polished.

combine both parts of the smoking pipe

Step 5

Let’s move on and render a stylized square tobacco smoke, which comes out from the pipe. First of all, form a group of rectangles of various sizes, overlapping each other and moving up and to the right from the captain’s figure. Now let’s move the squares a bit, aligning them towards each other. Select the bottom two squares and head to the Align panel. Set Align to Key Object and select the Horizontal Align Left function, to align both squares to the left side.

render a stylized square tobacco smoke

Step 6

Align other squares to each other by the left or right side if needed. When you’re satisfied with the result, select all the squares and Unite them in Pathfinder, forming a single object.

render a stylized square tobacco smoke 2

Step 7

Let’s make the shape smoother. Go to Effect > Stylize > Round Corners and set the Radius value to 7 px.

render a stylized square tobacco smoke 3

Step 8

Fill the smoke with greyish-blue color. Duplicate the shape twice and form a narrow stroke for the shadow with the help of the Minus Front function of Pathfinder.

render a stylized square tobacco smoke 4

Step 9

Apply a linear gradient to the created stroke, making it darker than the basic smoke shape. Select the shadow shape and take the Knife Tool (you can find it in the same folding menu as the Eraser Tool). Move the Knife across the shadow, making diagonal cuts at the corners. This way we create a nice shiny effect, something like a mirrored glass.  

render a stylized square tobacco smoke 5

Step 10

Although we're creating a flat-style image, it shouldn’t look too flat. We need to separate the objects from each other, adding more space and dimension. Simple shadows can help us a lot! Start from the smoking pipe by duplicating it and Uniting all the shapes of the created copy in Pathfinder, thus making a pipe silhouette.

Move the created object down a bit and fill it with linear gradient from brown to white, switching to Multiply Blending Mode and making a gentle shadow on the captain’s lower lip and beard.

put shadows in Multiply Blending Mode

Move on and put a shadow under the character’s moustache and nose, and also under the peak of his cap. Feel free to add more shadows where needed—under the ear or over his chest.

put shadows in Multiply Blending Mode 2

4. Form a Decorative Rope Frame With the Pattern Brush

Step 1

Let’s give our artwork a completed look by placing the captain into a thematic frame. Firstly, we need to make a stylized rope for our future brush. Start by making a small rounded rectangle with a bigger corner radius, so that it looks almost like an ellipse. Use the Rotate Tool (R) and set the Angle value to -30º. 

Select the shape and, holding down the Alt and Shift keys simultaneously, click and drag the shape to the right, creating a copy. Make sure you have the Smart Guides turned on (View > Smart Guides), so that the shapes snap to each other, making your workflow easier. Press Control-D to repeat the last action, creating another copy of the rope element.

make rope elements

Step 2

Make the side elements darker to alternate the colors of the entire rope. Now we need to make a bounding frame, which defines the repeating element, helping us to create a seamless brush stroke. Take the Rectangle Tool (M), set the Fill and Stroke colors to none, and form a square, crossing the middle parts of both side elements. Move the square behind all other elements (Shift-Control-[).

The Smart Guides will help you to be more precise, marking the center of the shapes and showing their intersection. Add a few minor details such as highlights and shadows to the rope, making it more detailed.

make rope elements 2

Step 3

Select all the created elements together with the bounding frame and drag them to the Brushes panel. Select the Pattern Brush and leave all options as default in the pop-up Options window.

create a pattern brush

Step 4

Let’s see our brush in action! Take the Ellipse Tool (L) and create an even circle around our captain. Duplicate the circle and, keeping both the circle and the captain selected, click the right mouse button and Make Clipping Mask, thus making the unneeded parts invisible. Select the second circle and apply the rope pattern brush that we’ve created. You can also take the smoke out of the Clipping Mask and place it on the very top (Shift-Control-]), making it pop out.

form a frame with the pattern brush

Step 5

Let’s add a simple paper ribbon to balance the composition. Form a rectangle in the bottom part of our frame and fill it with a sandy yellow color. Add two smaller rectangles of darker yellow on both sides of the ribbon.

make a ribbon

Step 6

Create a darker triangle between the edges of the upper and lower shapes, thus forming a fold. Select the side shapes, go to Object > Path > Add Anchor Points and drag the side anchor points that we’ve added closer to the center, making the shapes look like tiny flags.

make a ribbon 2

Step 7

Group all parts of the ribbon (Control-G) and go to Effect > Warp > Arc, setting the Horizontal Bend value to 20%.

make a ribbon 3

Step 8

Let’s Object > Expand our ribbon and add a few notches to make the paper look old and shabby. For this purpose, add three anchor points with the Add Anchor Point Tool (+), select the middle point with the Direct Selection Tool (A) and Convert it to corner. Drag the converted point down, creating a triangular notch on the ribbon.

make a ribbon 4

Step 9

Put some more notches here and there and move on to the background behind the captain. Let's add some depth to our image by placing a dark blue gradient shape behind the captain (double-click on the captain or right-click and Isolate Selected Clipping Mask in order to edit the objects inside the mask). Speckle some tiny circles above the dark background, depicting a night sky. Add another rectangle behind the captain, making it a bit darker than the sky in order to form the ocean surface. Go to Effect > Distort & Transform > Zig Zag and set the Size value to 6 px and the Ridges per segment to 5. Make the points Smooth, thus creating an ocean wave.

render a night background

Step 10

Add several thin stripes for the waves and apply the same Zig Zag effect, creating smooth curves.

render a night background 2

Step 11

Let’s fill the empty space of our ribbon with some text. Make up a phrase and choose an appropriate font to fit in the composition. I’ve used the Amatic Bold free font, which you can get from Font Squirrel. Object > Expand your text, turning it into a vector object, and apply the Arc effect with 15% Horizontal Bend value. Switch the text color to darker brown in order to fit our image color palette.

add your text to the ribbon

If you notice that some parts of the text are crossing the empty space, just delete the unneeded parts with the help of the Shape Builder Tool (Shift-M) by clicking them while holding down the Alt button.

add your text to the ribbon 2

Step 12

Glorious! Now we have only some minor details left to add to give our artwork a more interesting and completed look. 

First of all, let's Copy the captain’s beard and Paste it in Front (Control-C > Control-F). Open the Swatch Libraries menu in the Swatches panel, go to Patterns > Basic Graphics > Basic Graphics_Textures and find the Hatching texture. Apply it to the beard copy, imitating separate hairs. Use the Scale tool (S) to reduce the size of the texture elements by setting the Uniform Scale value to 70% and ticking the Transform Patterns checkbox. You can switch the textured shape to Multiply Blending Mode and reduce its Opacity in the Transparency panel to make it more true-to-life.

add hair texture

Step 13

Finally, let’s add a soft noise effect to our picture, making it more grained and textured. Start by placing a square of a size of our artwork on top of all other objects. Fill it with light greyish-yellow color and switch to Multiply Blending Mode. Then go to Effect > Effect Gallery > Texture > Grain. Set the Intensity to about 72 and the Contrast to 53 and select the Sprinkles Grain Type. This way you get a nice gentle grain effect.  

add grain filter to make a noise effect

Land Ahead! We’ve Finally Reached It!

Great job, mateys! We’ve successfully created a funny stylized captain’s portrait, using only basic shapes and effects. I hope you’ve discovered some new shores and destinations for your creativity and will use the described tips and tricks in your future artworks. Good luck!

funny stylized captains portrait final result
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