So, in my estimation, it looks like, you would just take the image you wanted to mask as the hair, and then just place it along the hairline? I guess the issue i have is making it look organic, like in this image. Can i get an experts opinion?
Compositing can be more difficult than it may appear. At least if you are seeking a believable composite. I think your sample is okay, but not great. Some angles aren't really correct and the shadowing/lighting could be a bit better. But it's not a "bad" composite overall.
You can easily find thousands of examples related to poor compositing.
Just a couple from the link above...
These are generally "bad" because aspects such as shadows, lighting, angles, scale, perspective are all critical to match in a good composite. Not enough attention to these aspects causes element to clearly appear as though they are from different sources while the goal is to make it all look like things are from the same source.
To be fair.. at times being a "bad" composite is the entire goal.
There are quite a few online tutorials regarding compositing with Photoshop. Just a few....
Even Adobe's own help pages offer a tutorial:
While the actual cutting and combining of layers within Photoshop is not a difficult task. Overall difficulty comes from attention to detail. The more you can match lighting, angles, perspective, etc, the better a final composite will be.
Have a few separate complete pieces of proper plants or leafs as images with transparent background. Have several copies in different sizes and rotation angles (see NOTE1). Place them until you have enough, do not clip a maze, because the edges would be wrong.
You may need also pieces which are squeezed vertically or horizontally to simulate watching direction which isn't straight on the face.
Insert a shadow between the assembled plants and the face.
Spraying with symbol sprayer (Inkscape, Illustrator) or would speed up the process, but the final touches very likely must be done manually.
Another way is to draw multiple strokes in Illustrator and apply a Scatter Brush, which contains one or more flora items.
NOTE1: Rotation and scaling variations are selectable options for symbol sprayers and scatter brushes, manual rotating and scaling is not a must.