For the first step you should draw just the outline of Shikamaru's head and shoulders. Draw guide lines on his face to help you position his facial features.
Next draw his facial features, earrings, hair, and the outline for his vest. The top of his eye should be about where the top guide line is.
This step seems harder than it really is. Draw the beginning of his hairline which is like a wide "M". You can now begin drawing out more of his vest and shoulders.
Now you just need to define his hair line by making little zig-zaggy lines. Make sure not to space them out too much and don't make the lines too long. Also draw his hairband which is basically just two curved lines. You can also erase the guide lines if desired.
Now we just need to make the detail on his vest. The line down the middle of his chest is kind of shaped like a "Y". Now draw the curved lines on the collar of the vest and two circles just below the shoulders.
For the last step draw in the two pockets on Shikamaru's vest, the design on his left arm and the forehead protector on his right arm.
Thanks so much for checking out this tutorial! Please leave a comment telling me what you think and what I can improve. Also feel free to leave a suggestion on what I should make a tutorial of next! :)