Since I brought up that there are different types of AI or machine learning, I didn't want to leave it at that. So that anyone can look into it themselves, I asked my friend, Dr. Shearman about this. My questions were:

1. Is AI really the right tool, or would a more deterministic set of algorithms be better?
2. What methods of training an AI on the images be best?
3. What general class of AI would this fall under?

His responses were:
1. Yep, AI or ML (machine learning) is the right tool for this task.
2. Assuming you don't have any a priori structure to your images, I would try fine tuning a vision language model.
3. Vision language models are what you want. Inputs: (image, text) -> text. Such that (img, "does your image contain a person wearing a kilt?") -> "yes"

He went on to explain that there is a way to segment the image to focus only on the tartan, and use other image processing for the identification. You can also fine tune the model at the final stages of development on targeted examples, which requires a lot of labeled data. He also stated that a small convolutional neural network might be able to solve this problem directly.

Much of this is specialized knowledge that I would have to look into more to understand (like what a "convolutional neural network" is). So, I think I'll leave it at that for folks to investigate if this is really a problem space you find interesting. I don't know if the finished product would justify the cost in time and money to develop, but there we are.