Go online and find a photo/template of a roller skate you like. Print it out in the size you want, cut it out and use it as a template to cut around with a sharp knife. Roll out your cookie dough, place the template on and cut around it. Then bake as usual.
That is how I would do it. Hope that helps.
Here are some pictures.
Teri, Ontario, Canada http://www.TeriLovesCake.ca