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Plan your design carefully. Trace your design with pencil. Use a thin-tip permanent marker. Let the shoes cure for a day. Set your design with waterproof acrylic spray.
Because you are planning on permanently altering your shoes, ensure that your design is one you’ll want to wear for some time. Also consider all the different places you wear your shoes. You may want curse words on your Converses at a music show, but not when you meet your new girlfriend’s parents.  If you’re feeling stuck for ideas, take a look at your room. What kinds of colors and patterns do you like? Is there a favorite band or collectible you love? Drawing inspiration from your own life will ensure your Converses reflect you. You can never go wrong with classic patterns like stripes, polka dots or chevrons. Once you’ve settled on a design you like, take a pencil and outline your illustration on the canvas top and/or rubber toe of the Converses. Designs on the rubber of the toe can stand up a bit better over time than the canvas, but it’s up to you. By tracing with pencil first, you can edit your design as you see fit. If you decide you don’t like your idea and want to start over, you can even wash your Converses on low in your washing machine to wash the pencil out. When you’re happy with your pencil outline and want to move forward, be sure to draw with a permanent marker so your design will last. Thin-tip permanent markers will provide a little more control and bleed less if you are drawing on canvas.  Keep in mind that all colors will fade a bit over time. If you prefer a vibrant look, be sure to use very bright colors from the start. They may become more muted. It can be helpful to color with lighter markers first. If you make a mistake, you can always fix it by coloring over with a darker marker. When you are finished, let the Converses cure for at least 24 hours so the ink can fully sink into the material and set. During this period of time, it makes sense to place your shoes in a clean, dry place where you won’t accidentally get water on them. It is critical to set your new design with waterproof acrylic spray such as 3M Scotchgard Fabric Protector or Nikwax Fabric Waterproofing Spray. These will weatherproof your illustration. If you don’t have access to these sprays, you can rub the canvas of your Converses with beeswax. Then set the wax by blowing it with a warm hairdryer to seal your design.