Sakura could design Naruto's new clothes. She has shown an interest in fashion and is quite creative. She might make him something that combines both practicality and style, knowing Naruto's active lifestyle as a ninja.
New clothes can also be a way to show Naruto's growth in different aspects. For instance, if he's given clothes that are more in line with the traditions of the Hidden Leaf but with a unique style, it could mean he's becoming more in - tune with his village's heritage. This could lead to him being more respected by the elders and villagers. And if his new clothes are made by his friends, it would strengthen his bonds with them, and his character would become more centered around the importance of friendship and community.
I think it could be an old, retired ninja who has a passion for fashion. This ninja has seen many battles and knows what kind of clothes would be practical for Naruto. He would use his experience and knowledge to design clothes that are not only stylish but also enhance Naruto's abilities. For example, he could add some special seals into the fabric that can store chakra or protect Naruto from certain types of attacks. And he might also incorporate some elements from Naruto's past adventures into the design, like using the pattern of a beast he once fought against.
Jiraiya might comfort Naruto by sharing his own experiences. He could tell Naruto about the times he faced difficulties and how he overcame them. For example, he might talk about his training with the toads and how he grew stronger through perseverance.
Sakura could design her new clothes. Since Sakura has an eye for fashion and also knows Naruto well, she could come up with something both practical and beautiful.
One possible reason could be that Naruto feels he has learned all he can from Jiraiya at that point. Maybe he wants to explore his own path independently and test his skills without Jiraiya's constant guidance.
Perhaps in this fanfiction, Jiraiya discovers that Naruto is going to be the cause of a major catastrophe in the future. He might have seen a prophecy or some sort of sign that convinces him Naruto has to die to prevent this. It could also be that Jiraiya has been misled by false information about Naruto, which makes him think that Naruto has become an evil force that needs to be eliminated.
One possible reason could be that Naruto feels he has learned all he can from Jiraiya at that point. Maybe he has reached a level in his training where he believes he needs new experiences and challenges that Jiraiya can no longer provide.
Their relationship would be very strong. Jiraiya would see Naruto as not just a student, but also as a connection to Minato. He would be strict but also very affectionate. Naruto would look up to Jiraiya as a father figure, since he never really had one. They would share many adventures together, with Jiraiya teaching Naruto about life, love, and ninjutsu.