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I'm trying to replicate the chequered boxes on the following image (sorry for really low-res)

enter image description here

Notice how the squares distort / warp with the shape of the path.

I can create the chequered boxes easily as a pattern in Illustrator... I then pasted them into Photoshop and tried the Warp tool (but this really didn't go very well).

Perhaps it is a better idea to create some form of Brush in Illustrator instead?

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A Pattern Brush could certainly do it. After applying it to a path, you could then use the Width Tool to change the thickness of the brush stroke.

Example

enter image description here

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