Id like to "zip" both sides of a portable external hard drive case with a drive inside and its connector cord (external drive port to USB-C) protruding out.
Its to keep the drive safer or cushion the fall if it falls accidentally.
After looking at the picture a little closer, there’s not much room in that case for the rigid portion of the USB connector when it’s plugged in. I think your best bet would be flip the drive so the USB port is facing up (towards the end of the zipper) and plug in the cable and zip the case like 80-90% closed. Good luck!