Alphabet Headcanon. S,H,I,N,O,B,(I)
Generally, the clothes Itachi will wear are comfortable clothing he can move around in. He doesn’t want anything too confining. Both in his past and presence, most of his clothing is dark, mostly because he has a bad habit of blending into the shadows and that weird but useful habit will never chance. Even though he doesn’t wear his ninja sandals anymore, he does wear boots. No matter what he wears, he doesn’t make a sound when he walks. And he has a habit of wearing gloves. This is merely a habit, it keeps his hands protecting from damage and doesn’t leave fingerprints.
H- Home/living quarters headcanon
In my modern verse, Itachi lives in a private apartment in Tokyo. His space is a little too big for his liking since he was always used to living in the Uchiha compound with his family. However, even despite that, his home is always clean. He isn’t a neatfreak but Itachi himself doesn’t make messes that he doesn’t clean up. If he cooks, he simply cleans as he goes along, and dishes are washed directly after he’s eaten. Though he’s gotten used to the apartment, Itachi is often found on his balcony, looking up at the night sky or simply standing in the rain. It’s like his personal thinking space.
I don’t know what most people consider quirks but Itachi isn’t the most normal person, at all, even by social standards. He’s incredibly polite, even to those who insult him. But I suppose a quirk would be his sense of humor? He doesn’t get slang, or even appreicate dirty jokes. But you give him the lamest joke or pun and he’s practically cackling like a hyena.
Itachi is one of those friends you won’t find many of. He’s a great listener, and he’s reliable and trustworthy. He’ll do anything to protect you and make sure you’re happy. You see, Itachi didn’t have many friends as a child and even when he did, he never gave them his full trust. But even then, he tried his best. Once he’s learned to trust you as you will come to trust him, you’ll learn that’s an awkward dork of a genius who just wants to have strong bonds and find a semblance of normality, of what it’s like to surrounding yourself with people who care for you. If you call him at 4am and want to talk, he’ll stay up to listen, to give advice when needed and he might even come over with your favorite snacks and movie just to cheer you up.
Itachi’s interest lay in what he can learn that he doesn’t already know. Teach him how to cook a proper meal, teach him how to knit, or how to make those delicious tarts you saw on t.v. Hell, teach him the meaning of flowers.
Itachi is a very particular eater. Textures and how easily someone will digest plays a very big part in his diet. Red meats are generally pushed aside, because he likes the leaner meats and more often than not, he’ll pick fish over meat, and tons of vegetables to go with his meal. He’s very partial to fruits and pancakes as well. Those are particular his favorite especially during the afternoon. He does indulge in a vast amount of sweets after the midnight hour, mostly his dango or more fruit.