Strange Headgear!

An ai image search gives me what seems to be ottoman such as this
Code:
https://commons.m.wikimedia.org/wiki/File:The_world%27s_leading_conquerors-_Alexander_the_Great,_Caesar,_Charles_the_Great,_the_Ottoman_sultans,_the_Spanish_conquistadors,_Napoleon_(1913)_(14783494732).jpg
 
An ai image search gives me what seems to be ottoman such as this
Code:
https://commons.m.wikimedia.org/wiki/File:The_world%27s_leading_conquerors-_Alexander_the_Great,_Caesar,_Charles_the_Great,_the_Ottoman_sultans,_the_Spanish_conquistadors,_Napoleon_(1913)_(14783494732).jpg
Yes, that’s more like it, a bit like a pumpkin :D
 
Looking at them. I dont' think they are Tam O'Shanter hats at all. They dont look they are from Europe. I agree with Gertrude but can't make out the second name.
 
I can't make out the second name either. I wonder if it would be possible to gently spread the paper to get a photo of what's written on the back of the second silhouette in full?
 
I can't make out the second name either. I wonder if it would be possible to gently spread the paper to get a photo of what's written on the back of the second silhouette in full?
I will ask. :)
 
I received the following message from Tim:

Thank them all please for their thoughts and efforts…
I don’t think we are there yet…but I too think the family might have a military connection…but not sure why two children have the hats and not others.
I will keep you all posted of any future findings.
Thanks everyone.
Tim.xx
 
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