Sidewalk Chalk for Beginners: Tools, Tips, and Tricks

Every time I spend a few hours on my hands and knees working on the sidewalks, I slowly climb to my feet and hear every joint in my body creak like an old rocking chair. This is what happens when you eat like shit, drink like a fish, and never exercise. Fuck it though. I like drawing on the sidewalks and if that means punishing myself physically for taking crap care of myself, so be it. I want what I want. What I want is to be a dope chalk artist.

If you want to be a dope chalk artist too, I want to help you get there. Fair warning: this is going to be long but I’ve tried to break it out into categories so you can more easily find the information you’re looking for.

Reference Images:

Obviously, you don’t NEED a reference photo unless you’re looking to recreate something. As a portrait artist, I use reference photos. If you want all the details in the world, look no further than this blog post about good reference photos. Otherwise, try to find something big enough to draw on, clear enough to see sharp lines and details, and well lit so you get a balance of lights and shadows.

Because I like to recreate existing images, I utilize the grid method to make my work as accurate as possible. I start by drawing a grid on my reference photo. I try to make sure the photo is big enough to see the details I need. Typically, I just color print a photo on a normal sheet of printer paper.

Finding a Space:

Did you know that there’s such a thing as good and bad cement? I never considered it until I started doing sidewalk chalk but there is an ENORMOUS difference in smooth cement versus asphalt or exposed aggregate (in time, frustration, amount of chalk needed, and general sanity). Do yourself a favor and find something smooth. If there are a bunch of little pebbles in it, you’re going to have a little less fun and have a harder time getting your image to look smooth.

If you don’t have a driveway or sidewalk in front of your house (like me), then wander around local parks, city sidewalks, whatever. Because chalk it temporary, it’s not considered graffiti. I typically try to avoid private property (unless I’ve been hired to do it).

I always look for a spot that’s close to a bathroom, where I can leave my shit out for five minutes without worrying about it getting stolen when I need to pee. Also, shade is everything. I’ll sometimes cart along a patio umbrella to spare myself the tortures of direct sunlight.

Before You Start:

GET YOURSELF SOME GOOD KNEEPADS. Just trust me. Have a couple old towels too, I use them to pad my hands, ankles, elbows, etc. You’ll find that if you’re out there very long you’ll be in all kinds of weird positions and a couple little hand towels are a godsend.

If you’re going to do a portrait or you’re gridding out your space, bring a yardstick or tape measure and a chalk line. Otherwise you’re manually drawing straight lines for your grid and, ugh, what a pain in the ass.

Sketching Your Design & What Chalk You Need:

What I do requires a detailed sketch, which I do with white chalk. Sketching will save you a lot of heartache down the road. If you mess up on a part of the sketch, bring along a sponge and some water. If you wet the sponge, you can do a small amount of erasing. Once you start laying down color though, this trick will be useless. Sooo…just take your time to get the sketch right.

There are a lot of different kinds of chalk but for sidewalks, I think there are three basic options, each with their own pros and cons.

  1. Normal Chalk

    • If you go this route, I just use standard Crayola brand chalk. You can get just white, a box of 6 or 8 colors, or a box of 16 colors. Whatever you choose, you’ll need a lot of it. This stuff wears down quickly on cement.

    • Normal chalk will give you nice colors that are bright and bold. Because it’s small, you can get real detailed. You can even use a pencil sharpener to bring your chalk to a point for extra fine lines.

  2. Sidewalk Chalk

    • Sidewalk chalk will last longer than anything else out there. Again, I just use Crayola brand. They come in big, bulky sizes and rarely have bold colors. They last longer because they are more dense but they do not provide much color saturation.

    • If you want your sidewalk chalk to look more bright and bold, you can soak it in water for about 10 seconds before you start drawing with it. You’ll need to do this repeatedly but it makes for some nice colors.

    • You won’t get a lot of detail with these because they’re big around.

  3. Chalk Pastels

    • This is what I typically use. Chalk pastels offer rich, saturated colors and are smaller so you can get pretty good detail. However, they are square so they can’t be used in a pencil sharpener.

    • I buy these ones. They’re more expensive than the normal chalk or sidewalk chalk and 1 box will get me through 1-2 portraits, depending on their size and what colors I need.

Blending Colors:

Blending is what will make your work come to life. To get your colors to blend, you have to layer them. I do a base color which smooth out with my hand. Do yourself a favor and get a box of latex gloves to wear on the hand you’ll be blending with (for me, it’s the same hand I draw with). They won’t keep your hands clean because you’re going to tear through a ton of them, but they will save your fingertips from being shredded up. Once you put your base color down, add small amounts of whatever other color you want to blend it with and using your gloved hand, rub over it. Start small and add more color as needed.

Other Random Tips You’ll Wish You Had:

  • If you’re laying out a grid, bring a or something to told the end of your line. Also, use it to keep your reference photo from blowing away.

  • Bring a bluetooth speaker, not headphones. You'r ass is going to get hella’ interrupted while you work. If you have headphones in, you’re going to have to keep pulling them out to chat with curious passers-by. Some artists hate this but I honestly think it’s super fun to have visitors. When they come, just work and talk…they want to see you work.

  • Wear clothes you can move in because you’re going to contort into some weird positions and if it’s hot, you’ll be sweating.

  • If you’re a lady with big ol’ boobies (or even medium ol’ boobies), wear a sports bra. Oh my god I can’t even tell you how glad I was that I wore one the first time I tried this.

  • Bring water, coffee, and snacks. You’re going to savor them.

  • Stand up and stretch frequently, you’ll hate yourself the next day otherwise.

When You’re Done:

Take a million photos, obviously.

When I get home, I use a vibrating back massager thing on my shoulders, lower back, ass, and thighs. About 30 minutes later, I take a long, hot shower then put on some PJ’s and spend the rest of the evening on my couch, massager on my back, cocktail in my hand, husband by my side, cat in my lap.

It’s punishing work and regardless of what you do, you’ll feel it the next day. It’s so, so worth it though. I LOVE doing big chalk pieces on the sidewalk. I love watching them fade, I love seeing people interact with them. It’s fun and rewarding and great way to get your name out into the world.

Am I Missing Anything?

If you want to know anything else about sidewalk chalk, I’m here to answer questions! Feel free to email me em@emnarts.com

None of this stuff will automatically make you a great chalk artist but it will save you some trial and error time.

YOU’RE WELCOME!!