Using regular chalks on simple surfaces as well as larger scaled drawings on streets and sidewalks as a second step can be a great way to start and simultaneously develop skills that will surprise beginners. A simple drawing of water with distant land on the horizon and a bright but perhaps cloudy sky may be a good place to start. Alternatively a simple still-life such as a piece of fruit sitting on a piece of a cloth with a contrasting color is also instructive. You can draw observing the natural setting, or from photographs taken when the light is just right. You can also put the photograph on your computer and cut out a section of it, and draw it after resizing and enhancing brightness or contrast. This is especially useful if you want to capture the image on a street or sidewalk drawing, perhaps as part of a Street Art Fair in your local community.
Whatever surface you are drawing on, whether white paper or colored paper or sidewalk or street, it’s important to remember that it will only allow so much chalk to cling to it. It may be useful to first draw in and blend with fingers or wipes light blues for water and sky and a little light green for the forest that is seen at low resolution in the distant horizon. Then you can add some sharper features with darker colored chalks, blending them also into the background at the edges.
In street or sidewalk chalk art, select a clean street or sidewalk area which is neither too rough nor too smooth. It’s probably important from the outset to use an artist’s chalk like Koss which has a great color selection and adheres quite well to street and sidewalk surfaces. For a street or sidewalk drawing which is almost always much larger than the expanded, printed photo you may be starting with, you will need to expand the drawing proportionately. You can use what is known as the grid system. For example, if you want to expand the photo into a 3 ft by 4 ft sidewalk or street image divide up the street into 12 1ft by 1ft squares. You will need a chalk line and a tape measure to mark off these 1 ft by 1 ft spaces in the 3 ft by 4 ft area you’ve identified for the drawing. Then cut up a copy of the photo or print you are using as the basis for your street art into 12 equal segments. You can actually cut them apart and adhere them lightly with glue to a cardboard surface and number them 1-12. Do the same with the 12 1ft by 1 ft squares in the street or sidewalk surface, and then, of course, don’t lose track of your orientation while you draw.
Drawing street or sidewalk art with chalks is hard work so get as comfortable as possible. In addition to the tape measure and the chalk line you may have already used, you’ll need hand wipes and good fitting plastic gloves which fit tightly but not too tightly. You’ll need multiple layer cardboard or perhaps plastic gardeners pads to sit or kneel on and or knee pads. It can get hot and sunny–so you’ll need sun screen, a hat, and water. I usually keep 4-5 bottles in a cooler nearby. Remember to take breaks as you proceed. You always need a little time to look at your art as it develops both up close and from a greater distance, photograph it. You also need the time to sooth sore muscles and stretch them out. This will also give you some perspective on how to sit, kneel or stand and change those positions now and then when working on applying chalks to the drawing. For some work you should remember that you can also tape chalks to sticks and apply chalk thus from a standing position. That’s hard to do for some of us and requires practice.
When you are ready to start, remember we’re doing one square at a time. I think it’s a good idea to pay a lot of attention to the inner squares first as these often contain the most difficult and interesting features to draw, particularly faces and eyes. If you get those right in the beginning, the rest of the work can proceed much more effectively especially from a psychological perspective. Take photos as you proceed and watch as your art develops. Later you can put the photos on your computer and reflect on how the total drawing evolved.
In applying chalks, circular motions in both ways are preferred. These surfaces will only take so much chalk and after that the excess will simply blow away in the wind.
Even those just beginning to use chalks can have a lot of fun with street and sidewalk art. Try it as soon as you feel comfortable using chalks. On the internet you will find many web sites describing street and sidewalk art with chalks, particularly in making drawings with unusual and sometimes humorous perspectives. You should look at many of these before you begin your own efforts. You can start by googling “chalk drawing.”