Where's Waldo

Should be really easy to kitbash. Any jeans and normal shoes, long sleeved shirt (you'll have to make a striped texture in photoshop but that should be easy, then just overlay blend the pattern over the texture file for the shirt) A beanie that sits on the head like Waldo's will be the hardest part but if all else fails take something like this

https://www.daz3d.com/bw-lucas-everyday-headwear-for-genesis-9

and add a dforce modifier to it and play with position and dforce settings until you get it to fall the way you want it to.

Hair I think something like this would work

https://www.daz3d.com/adamo-flip-hair-for-genesis-9-and-genesis-8-male

but really any short hair that has the flippy bit in the front to stick out from the beanie is what you want.

Finishing touches:

glasses - https://www.daz3d.com/glasses-set-4-for-genesis-8-and-81

cane - https://www.daz3d.com/old-man-poses-and-walking-cane-for-floyd-8

and if you want to go overboard with his gear from the first book, you could start with this backpack and build from there: https://www.daz3d.com/backpack-series-hd-nomad or look around for a messenger style bag that you see him depicted with more often.

The real challenge is then getting 200 other similar-looking models into your scene without turning your CPU into glowing lava!