Neoprene was the perfect material for this project. It's flexible, has a pleasant texture, and can be laser-cut. I own a $370 40W laser cutter from China. So far, this machine has been very reliable and awesome, with a sizable cutting area of 12" by 8". However, I wanted to make my headband out of a single strip of adhesive neoprene (linked under components). I found that the 99th percentile for head circumference is about 25", so I had to laser cut a 50" strip that would be folded in half. The strip is only 1.5" wide but the 50" length is much longer than the 12" I had to work with.

I used Illustrator to plan out the entire strip.

Then, I split up this file into two 11" sections for the motor windows, and a smaller section with the wire slot. The motor holes had to be aligned very precisely to one another, so I added a tiny mark in the top-right corner of the first section so I could put the laser. All of my laser cutting files, including the original Illustrator source, are available for download as a zip under Files, and on the project GitHub at https://github.com/andrehchs/wgps.

After cutting a 55" inch strip (for some leeway), I taped it to the bed of my laser cutter with some masking tape and started the cutting process. Once I cut out the first set of motor holes, I removed the masking tape, adjusted the neoprene strip such that the laser was aligned with the far edge of the first cut, loaded up the next cutting file and cut the next set of holes.

I used the LaserDRW 3 software that was included with my laser cutter, by importing the files as PNGs and selecting "Cutting" under the dropdown menu in the top right of the Engraving dialog. I used 1200 PPI bitmaps. I'm sure there are ways to cut vector files with a K40, but this method (of using absurdly high resolution bitmaps) worked fine for me. 

I wasted some neoprene on stupid errors, but after two or three tries I was very happy with my results and the motors fit snuggly in their sockets.