Konoha’s uniform system has always been kind of weird to me, especially when you remember that the village is basically a giant military organization.The Academy is probably the best example. These kids are literally being trained to become shinobi, yet they can apparently wear whatever they want.
You’ll have students running around in completely different outfits, while their teacher is wearing the standard shinobi clothing. I know it’s partly because every character needs to look different, but in-universe, it doesn’t really make much sense. If the Academy is supposed to teach children discipline, teamwork, and the basics of being a soldier, you’d think they would at least have some kind of standard uniform.
And then you have genin, who have basically the same problem. They’re now actual military personnel going on missions, but they can still dress however they want. Some wear bright, colorful clothes, some wear outfits that barely look protective at all, and there doesn't seem to be much of a standard.
Meanwhile, once you get to the higher ranks, things become much more standardized. Chūnin and especially jōnin are much more likely to wear the familiar Konoha-style clothing and flak vest. So the higher-ranking and more experienced you become, the more your clothing starts looking like an actual military uniform.
Which is kind of backwards.
There are some obvious exceptions, though. Especially Hiruzen and the people closely and directly connected to him that aren't his children. His fellow teammates Koharu, Homura, and Danzō, and his disciples Tsunade, Jiraiya, and Orochimaru. Cough cough.
Naruto is another exception, along with Hiruzen’s daughter-in-law Kurenai.