I've been monkeying about with the OSR dungeon annual, working on wilderness maps for a VTT application. The OSR style doesn't come with anything built in to show elevation changes (unless I've missed it), so I built a couple of tools for that, with... mixed results.

The first tool is a simple contour line. The second uses the "line style" property from the custom tool properties box (something I've never really even noticed before). I selected 'Stair Case (for V wide line)' to create the look of an escarpment with a series of fine lines showing the gradient between elevation levels on the map. It doesn't produce the same quality you'd get from a hand-drawn escarpment, but it's not completely awful either -- just a little too perfect and regular perhaps.

I also added a slight glow to the water to set it off a bit more and pulled in some trees from one of the overland styles (I have a thing for tree symbols that show the trunk; in a VTT it can be very important to know where the trunk is rather than just showing the tree top).

OSR wilderness project

Tips and feedback is always appreciated.