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Go with the Brush Tool, Not the Pencil
Invest in a good sized tablet. It will help you to do illustrations with precision and also give you a variety of contours, pressures, and strokes while painting. Changing these attributes randomly and repeatedly while painting the illustration will help to create the hand-drawn look. In some cases, stretching some of the points in the strokes can also help create the desired look.
Avoid Using the Gradient Tool
The gradient tool gives the image an unnatural look because it is nowhere close to what you can get with hand painted illustrations. Instead, to add shades to an object, simply use the pencil tool, with hairline thickness, to draw the desired shape of the shade and fill it with a slightly darker color. Remember to delete the strokes after the shading is done.
Don’t Mix Mediums
In an illustration, don’t add other mediums like photographs or fonts into the mix. Unless it is a part of the site which is specifically meant for it, like in a portfolio or a company logo, and must appear in its original style, do not mix mediums in your illustration. Even when you need text in buttons or titles, consider drawing it by hand and avoid duplicating letters where possible. Randomness and detail adds character to the illustration.
To help make drawing fonts easier, write the text in a font of your choosing and trace it by hand. This will also help keep to the natural hand-drawn look of the illustration. You can also try your hand at creating your own font.
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