He might seem more studious. Wearing glasses could give the impression that he's more into reading and learning new jutsu. So he could be seen spending more time in the library or with his sensei, trying to understand complex ninja techniques.
If the glasses are part of a new power or ability, Naruto might become a bit more cautious. He realizes that he has something valuable and that he needs to protect it. So he might be more strategic in battles, thinking about how to use his glasses - related power effectively while still maintaining his bold and fearless attitude that we all know and love.
He might become more self - conscious at first. Naruto is usually very confident, but wearing a dress would be something new and out of his comfort zone. So he could become a bit more reserved until he gets used to it.
He may develop a more reckless side. Feeling like he has something to prove now that he has this 'disability' of sorts. He could be more willing to take risks in battles, thinking that he has less to lose. This new - found recklessness could either lead to great victories or put him and his friends in more danger than before.
He might become more cautious. Tsunade is a more calculating ninja compared to some of Naruto's previous mentors. So Naruto could start to think before he leaps, rather than just charging into battle head - first all the time.
His personality would become more reserved. As an assassin, he couldn't be as open and friendly as he used to be. He'd have to keep his emotions in check to avoid being detected.
He might become more logical. Since robots are often programmed with certain algorithms, Naruto could start to think more in terms of cause and effect rather than just his usual impulsive ninja instincts.
Naruto's personality would become more brooding. He would be less impulsive and more calculating, like Batman. He might not be as openly friendly as he was before, keeping his thoughts and plans more to himself.
Naruto's personality might show a more serious side. Wearing a suit could make him feel more responsible, like he has to represent the Hidden Leaf in a proper way. So he'd be less likely to crack jokes and more focused on the task at hand.
Naruto's personality would likely become more patient. As a medic nin, he would need to be calm and focused during treatments. His impulsiveness would probably decrease as he realizes that any hasty move could harm a patient. He might also become more empathetic, understanding the pain and suffering of others on a deeper level.
If Naruto becomes a hunter nin in the fanfic, his sense of justice could become more complex. As a hunter nin, he'd be exposed to different shades of right and wrong. He might not be as quick to judge someone as he used to be. Instead of simply seeing enemies as bad guys, he'd start to understand the reasons behind their actions. This could make him more empathetic but also more calculating in his approach to dealing with threats. Also, his normally boisterous nature would likely be toned down to avoid attracting unnecessary attention.
Naruto's normally sunny and optimistic personality would likely become darker. He might be more brooding and less quick to trust. His sense of humor would probably take on a more sardonic edge as the power of Jack of Blades seeps into him.