From Male Stock to Female Vector Portrait in Adobe Illustrator


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This post is part of a series called Mastering Vector Portraits.
How to Create an Andy Warhol Inspired Pop Art Portrait in Illustrator
How to Create a Line Art Based Symmetrical Portrait in Adobe Illustrator

One of my biggest inspirations are drag queens, especially in my portrait work. In today's tutorial I'm going to show you how I went from a male stock image to a female vector portrait in a drag queen style. I'll start with creating a photo manipulation reference in Adobe Photoshop and then bring it over to Adobe Illustrator to work from. This is more an exercise in transforming a stock image to create a portrait unlike what you've started with. So let's get started!

"Make up" Tutorial

Before we start with the actual process, it's worth checking out a full facial transformation from male to female from a make up tutorial. Consider it a theory based lesson. This is my favorite make up tutorial on this subject as the drag queen, Manila Luzon, goes over why you need to apply shading and highlights here and there.

Step 1

I'm starting with a simple stock image of a male. I've choose this due to the symmetry in the face, the sculpted cheek bones and the fuller lips. The cheek bones and lips will be easier to manipulate to create a female look. With a bald man, it makes the transformation more dramatic as a bald head is very masculine.

I've duplicated the layer with the stock image on and then used Filter > Liquify on the stock image. I've brought the lips out and slimmed the bottom lip slightly. I've reduced the width of the nose and lifted the cheekbones further. I've then rounded the jawline and changed the chin so it's more rounded rather than a masculine square jaw.

Step 2

Time to start blocking out and "neutralizing" some of the shadows and features. I'll be using the Brush Tool (B) with a pale skin tone to block out the eyebrows and angles of the face.

Then using the Smudge Tool, I've blended the edges through out the face. I'm also trying to hide the Adam's apple, which is a dead give away on a man! I've then lowered the Opacity to create a more natural coverage.

Step 3

Using an off white, I'm going to start carving into the face where the highlights need to be. This is where I create the brow bone and thus where the eyebrows will go. I've increased the side of the eyelids to create a deeper eye-socket. Highlighting along the jawbone will help make the jawline less square.

Then lowering the Opacity to blend the color in.

Step 4

Smaller highlights now and deep shadows are placed around the face.

Smudged and blended in with a lower Opacity.

Step 5

Using a much darker color, let's create eyebrows, eyelines and creased as well as sculpting the nose to create a more female appearance.

Here we have it again smudged and blended in.

Step 6

Let's finish off with more highlights, smudge them and blend them into the face.

So the face may seen exaggerated, but you can see a definite difference between the original stock image and our drag queen. Don't worry about the coloring as this is just the stock reference we're working from and we'll change the colors in Adobe Illustrator.

Step 7

I'm going to set up my New document in Adobe Illustrator. I'll File > Place the stock image onto the artboard and place a white filled Rectangle (M) over the top set to Opacity 50%.

In the Swatches panel go to Open Swatch Library > Skintone and use the bottom six palettes.

Step 8

Time to create our initial base for the skin. Use the Pen Tool (P) to trace around the face and neck, including the ears. I always start with a medium skin tone and then build on the highlights and the shadows.

Step 9

Duplicate the base and then draw shapes with the Pen Tool (P) where the lighter areas will be. Then use them to Pathfinder > Minus Front from the base. Repeat this process until you've got the first skin shading shapes down. The fill color will be the same as the base and are set to Blending Mode Multiply, Opacity 5%.

Step 10

With the Pen Tool (P), create more shadows either side of the face and the nose/eyes/lips. Use a darker skin tone and then set it to Blending Mode Multiply and Opacity 10%.

Step 11

Duplicate the skin base and then use it to create a Clipping Mask (Ctrl + 7) with the Grouped (Ctrl + G) skin shading shapes.

Step 12

I'm not happy with the contouring of the face with what we've got here. So I'm going to modify the dimensions. First, to be safe, duplicate the Clipping Mask group and hide it.

Use the Lasso Tool (Q) to select the areas you wish to change and then use the Free Transform Tool (E) to enlarge or shrink the selected area. Alternatively use your arrow keys on your keyboard to nudge your shapes.

Comparing the initial face shading to the new contours you can see I've increased the brow bone area, moved the lips and chin upwards and created a more slender face to remove more of the square jaw. It is turning out more cartoon in appearance, but remember that drag queens are exaggerated female illusionists.

Step 13

Create a transparent radial gradient and use it to fill shapes for the highlighting. These shapes will be set to Blending Mode Screen, Opacity 25%. Once done, place the shapes within the Clipping Mask group.

Step 14

Duplicate the skin base and then fill it with a reversed transparent radial gradient as shown below. This will be set to Blending Mode Multiply, Opacity 20%. This will help darken the neck and around the sides of the face.

Step 15

Time to add more refined shading with smaller shapes in the key areas. Use a darker shade and set it to Blending Mode Multiply, Opacity 10%.

Now for some more bold highlights with the highlighting radial gradient. Set these to Blending Mode Color Dodge, Opacity 20%.

And then more shadow defining the deepest shadows with the darker shade. These are set to Blending Mode Multiply, Opacity 20%. It is a juggle between adding highlights and shadow to get the contrast right.

Step 16

Let's add some subtle coloring into the face by filling three circles created by the Ellipse Tool (L) with transparent pink radial gradients. Set these to Blending Mode Multiply, Opacity 10% and then add them to your skin shading Clipping Mask group.

Step 17

I've already built up the shading on the lips, but now it's time to add color. I've done this by drawing around the lips and then using the Appearance panel settings below. Treat the lips as part of the skin, then apply color as if you're applying make up to create elements which don't appear to be floating on top of the skin, but are more part of the skin.

Step 18

I'm going to add further details to the lips by using a dark skin tone and setting it to Blending Mode Multiply, Opacity 10%. These shapes are more focused at the corners of the mouth and at the parting.

Step 19

Using the skin highlighting radial gradient, use the Blob Brush Tool (Shift + B) to add small shapes around the lips where the light would catch the slight creases. Group them (Ctrl + G) and lock them to add further shapes on top. Set these shapes to Blending Mode Screen, Opacity 50%.

Repeat the same with a darker color for the shaded areas of the lips. These are set to Blending Mode Multiply, Opacity 10%.

Step 20

To add a slight gold shimmer to the lips, add shapes at the top and bottom of the lips with a golden yellow transparent radial gradient set to Blending Mode Color Dodge, Opacity 40%.

Step 21

Now to start working on the eyes. Using the lightest skin color, draw shapes for the whole eye area and then for the eye ball. Set both of these shapes to Blending Mode Screen, Opacity 60%.

Use the Ellipse Tool (L) to draw an even circle for one eye and then duplicate it and move it into position for the other eye. This will ensure both are the same size.

Step 22

Duplicate the eye circle and eyeball shape and create a Clipping Mask (Ctrl + 7) within a Clipping Mask out of Compound Paths (Ctrl + 8) of the eyes and eyeball shapes.

Step 23

Add shading and color at the corner of the eyes and waterline and then around the eyes. Eyeballs are round, so the shading around the top and corner will help emphasis this. First apply a dark brown fill along the waterline and corner and set it to Blending Mode Multiply, Opacity 10%. Continue with the same fill and settings around the eyes and lid crease. Then with a red transparent radial gradient, add shapes in the corners of the eyes set to Blending Mode Multiply, Opacity 50%.

Step 24

For the eyes, I've taken advantage of the Appearance panel to create an outline around the iris and then to create the pupil. I've mixed several shades of browns and Blending Modes to create this effect.

I've then applied two transparent radial gradients. One towards the top to emphasis shadow on the iris and then one towards the bottom to add a golden glow.

Step 25

I'm going to add further contrast to the eyelines and crease by adding a dark brown fill set to Blending Mode Multiply, Opacity 40%.

Step 26

Then use the highlighting gradient to push the contrast on the eyelid, brow bone and corners of the eyes. Set these shapes to Blending Mode Color Dodge, Opacity 30%. This will also work well as a base for the eyeshadow... because drag queens love a bold lid!

Using a transparent radial gradient which goes from emerald green, to lime green to orange, draw shapes around the eyes and set the shapes to Blending Mode Multiply, Opacity 100%. This reminds me so much of the colors I used as a teenager!

Step 27

I'm going to shape the lips further before I continue with the eyes. I'm going to use the same Lasso Tool (Q) process to modify the shape of the lips. Remember to unlock all the layers you need to modify.

This will give the mouth on the portrait, more of a pout!

Step 28

To draw the eyelashes and eyebrows, I'm going to use my Width Profile brushes with the Paintbrush Tool (B). The top lashes will have a dark brown stroke, Width Profile 4 brush, 3pt Stroke Weight and set to Blending Mode Multiply, Opacity 90%.

The lower lashes will use the same settings apart from a Stroke Weight of 2pt, Blending Mode Multiply, Opacity 50%.

And the eyebrows use the Width Profile 1 brush with a 2pt Stroke Weight set to Blending Mode Multiply, Opacity 50%.

Step 29

Using the skin highlighting gradient I'm going to add a reflection on the eyes set to Blending Mode Screen, Opacity 60%. Then with the same color, add strokes around the water line and corner of the eye.

Step 30

I'm going to add an inverted transparent radial gradient around the face set to Blending Mode Color Burn, Opacity 20%. This is to help add contrast to the face an to help narrow it's appearance to create a more feminine look.

Step 31

Our face is now complete and although this is just an exercise on creating a male to female portrait, let's make it look a bit more presentable. First change the background color to a dark green, to compliment the eyeshadow. Then add a shape with the Pen Tool (P) around the hair line.

Step 32

Use the Width Profile 1 brush and the Paintbrush Tool (B) to add strokes around the hairline with the same dark green.

Then drape some strokes across the forehead, ears and neck to show a hint of long flowing hair.

Step 33

Use a lime green stroke and the Width Profile 1 brush and a 2pt Stroke Weight to add highlights into the green. If you're adding strokes near the hairline, remember to add them in the same direction as the hair to make it look more connected. Set these strokes to Blending Mode Screen, Opacity 10%.

Step 34

Finally use the Blob Brush Tool (Shift + B) to add strokes on top of your hair highlights with a lime green transparent radial gradient. Set these shapes to Blending Mode Color Dodge, Opacity 40%.


This has been a different sort of exercise for me in terms of creating a portrait, which I've learnt a lot more than I anticipated. Although I felt confident in creating a female appearance, transforming a male to a female has been a lot of trial and error to come up with a result I've been happy with. I've learnt more about placement of shading to create a feminine look and more importantly, I've had a lot of fun along the way. Try it out yourself and experiment to altering stock.