Connecting Soft goods to Plastic pieces

For a prototype, you can simply use Heat 'n Bond ultrahold from Hobby lobby. Laser cut to shape and iron into place, it holds with great strength.
For industrial purposes my preferred supplier is Bemis. You can sew through generic plastic at film thickness of 0.25mm. Yet you will create tears in the long term so I suggest just using holes and if you need waterproofing covering these up with glue/epoxy.