Kendall Plant is a designer, content creator, and art director whose unique creations incorporate nature, street photography, and even skulls. She works at Adobe as an associate creative director.
What you'll need
Plant opened a photo for reference and reduced its opacity. She used Control+R (Windows) or Command+R (macOS) to show the rulers, dragged a guide to the center of the model’s face, and locked the image layer.
Next, she selected the Curvature tool and clicked to create anchor points to draw an outline around the left side of the model’s face. The Curvature tool creates geometric curves automatically, so she didn’t need many anchor points. To create corner points and straight lines, she held the Alt (or Option) key as she clicked. To finish the shape, she clicked the original anchor point while holding Alt/Option.
With the shape selected, Plant used the Reflect Tool (“O” on her keyboard). She clicked on the center guide to set the reflection point. Then, she clicked on the shape, held Shift+Alt (or Option) as she dragged a reflected copy of the face shape.
Plant chose the Selection tool (V) and Shift+clicked both sides of the face. In the Properties panel, she chose Unite from the Pathfinder options and changed the fill to a warm brown color with no stroke.
Plant continued to draw facial features, sunglasses, and jewelry with the Curvature Tool while using the reference image to check proportions as needed.
As she worked, she reflected shapes across the center guide, united them, and changed the fill colors. She toggled the guide visibility by pressing Control+; (Windows) or Command+; (macOS), on her keyboard. She then hid the photo layer before adding hair in the next step. If the Curvature tool inadvertently interacts with other shapes, locking the paths within the layer can help to prevent undesired results.
To draw the hair, Plant chose the Ellipse tool and held Shift+Alt (or Option) as she dragged out a circle from the center of the face. Then, she filled the shape with dark blue and used Shift+Control or Command+[ to send it behind the face.
With the hair selected, she chose Effect > Distort and Transform > Zig Zag and experimented with the settings before settling on the effect she liked.
With the hair selected, Plant chose Object > Expand Appearance to convert the zig zag path to a shape so she could customize the hair with the Shape Builder tool.
To create a layered look, she held Alt/Option as she dragged to create overlapping copies of the hair, then used the Selection tool to select all the copies. Next, Plant selected the Shape Builder tool and held Alt as she dragged to remove the additional sections of hair outside of the original shape. Finally, she changed the fill color of the individual sections of hair.
To create a shadow, Plant used the Curvature Tool to draw a crescent shape, filled it with black, and reduced the opacity. Then she selected the shadow and the face and used Shape Builder as described in the previous step to trim the shadow that extended off the face.