I think I've mentioned that in my head-cannon Pokey Pierce is the town rapist right?
I tried to make Scootaloo look as much like a homeless child as I could. If you type in "homeless children" on a Google image search you'll either get a very theatrical looking Oliver Twist or little African children with bloated bellies. I figured having her wear somewhat ill-fitting clothes that aren't quite adequate for the weather and no hat or gloves would do the trick.
Yes, I'm still convinced Scootaloo is homeless... Homelessloo.