Ryan is required to wear uniforms to his kindi every morning. Therefore, from Mondays to Thursdays, he will wear the uniform on the left while on Fridays, it will be the orange + white t-shirt which I personally think is much smarter.
I took the photos on a Thursday and a Friday just before "unloading" him at the kindi. And yes, when it comes to taking his photos, he's very cooperative, even early in the mornings.