Naruto i think doesn't wear it because 1. So after war he turned 17 and we see him with hair cut and black new outfit so i guess he probably wore outfit in photo until 18 unless he changed outfit then the leaf change. Here's a breakdown of what they all wear and what i think are possible reasons for it:
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So characters don’t wear uniforms.
More interesting than a goth phase, naruto rocking guy and lee’s green jumpsuit was a bit of filler that we could have done without.
Every time there's a conflict he doesn't have time to put it on; At first his top is white to show he's still a good guy. The government of the hidden leaf village is made up of the hokage, the village elders, an advisor, and the jonin council. Well they didn’t have the leaf headbands until hashirama was hokage and he is shown wearing it.
There's much to know about why the hidden leaf village's citizens. The 5 best & 5 worst costume changes of all time. Kakashi didn't even start wearing his till he was an adult. The vast majority of characters in the shoe don't wear uniforms.
Right now he's in sasuke's bitch mode thus he's not allow to wear it.
Oil (油, abura) the reason why jirayia wears this symbol on this headband rather than the leaf symbol is to show. Naruto and the current kages are maintaining an era of peace. This could explain why nagato, who performed the technique near the leaf village, couldn’t resurrect jiraiya, whose body was far away from there. So clans have there own style of uniform like most leaf shinobi’s wear the jumpsuit that’s either blue or navy blue or black with the chunin vest.
Naruto has to be in his trademark running suit looking thing. The symbol on jiraiya's headband translate to. Of course, this means that the series protagonist naruto uzumaki has to have a wardrobe change every now and then, whether it's being done in a sequel or. Government in the hidden leaf village.
So, he is no longer required to wear.
You see the cloak only let naruto wear it when he's in badass mode. After the conclusion of the third great ninja war, jiraya was required to retire officially from his position as a leaf shinobi. The main naruto cast members undergo countless. Loose top for when he needs to use his wings, the rope to hold his sword;
Later on his top is no longer easy to drop becausehe no longer has curse mark wings. He went straight from there to the leaf, so he must've put it on shortly before he left.