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Is there any way to add an outline to a brush so that when stroking a path it will give a sense of depth and layering where the path overlaps?

As an example, here is an image of footprints. How could I add depth so that you can tell which footprints came later on (i.e. on top of other footprints) enter image description here

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I'm going to answer this question based on the comment thread that happened on a deleted answer, where Sean said:

Thanks, but what I mean by depth isn't the bevel and emboss 3D, I just meant layering; how it makes one footprint look like it's on top of another.

There are numerous ways to create a sense of "depth". As Scott mentioned, opacity is one technique. Any elements towards the bottom would have a lower opacity and elements stacked on top would have a higher opacity. The only draw back is that earlier footprints may be difficult to see and eventually, you will reach a maximum opacity.

Another alternative is to use different layers of footprints (separate the footprint paths based on walking from point A to point B.) Then you can add layer effects to emphasize depth. This includes drop-shadow and stroke. This approach takes a little bit more work, but you'll have more control over the result.

In the end there isn't a one-click solution that'll make your dreams come true (yet). for now you'll have to do some manual work to achieve the depth that you want to see.

Something else I might suggest is using less footprints overall, as it looks pretty cluttered as-is.

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No, but you could stroke paths individually as 'subpaths' instead, then apply a layer FX or a layer style for shadows or an outline.

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Paint on a layer by itself and lower the opacity of the brush.

Having a tablet such as a Bamboo or Intuos would allow you to control opacity as you paint, lending to the "overlapping" impression more.

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you may define your own brush, by keeping the strokes black and middle area light grey. I have just tested it, hope it will do the trick for you.

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just color them differently: darker to lighter. LIghter being at top.

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