Here is a noholds barred, all secrets revealed, tips and tricks packed walkthrough of how to create a pen and ink styled stipple shading effect in ArcGIS Pro. I'll also show how to save it to a style so it can be easily reused for other layers.
Here is the source for that cool layer I'm working with: http://www.projectlinework.org/
Here is the full Pen and Ink style, if you just want to dive right in and don't care how it works:
https://esristyles.maps.arcgis.com/h...

Check out some other social channels where I share howto's and updates on random map adventures:

http://adventuresinmapping.com
https://www.esri.com/arcgisblog/auth...
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