Itachi's Appearance

Despite his status as an infamous shinobi, his appearance was not the most intimidating, apart from the intensity of his eyes. While living in Konoha, he would regularly have a gentle and caring look in his eyes, especially directed towards his younger brother. After joining Akatsuki, he would regularly have a stern look to them.
He, like all members of his clan, possessed dark gray eyes, black hair that hung near his cheeks to frame his face and a long ponytail in the back of his hair; later obscured by his Akatsuki cloak after joining the organization. Being brothers, Itachi and Sasuke had a similar appearance, so much so that Naruto nearly mistook Itachi for Sasuke when they first met, but with subtle differences. Itachi's hair color appeared slightly duller and with a softer flow to it; his skin was also slightly darker. Itachi's most distinguishing characteristics were the long pronounced tear troughs under his eyes.
When he lived in Konoha, his casual clothes would consist of a black Uchiha shirt with a large Uchiha clan symbol on the back, and black pants with a weapons pouch strapped to them. When on duty, he would wear the traditional ANBU uniform, although he was never shown wearing a mask. As a member of Akatsuki he wore the traditional Akatsuki cloak and usually kept the center of it buttoned down, as well as a slashed Konoha forehead protector. At other times, he would unbutton the top half of his cloak and rest his left arm there, rather than in the sleeve. After his cloak was incinerated by Sasuke's Kirin during their fight in Part II, it was revealed that he wore similar clothes to that of the rest of the Akatsuki underneath it consisting of a blue V-collar T-shirt (where as most other Akatsuki members wore a sleeveless shirt) and blue pants with a body mesh under the T-shirt, and a white sash around his waist on the outside of the shirt much like a tunic. Like almost all members of Akatsuki, he wore the headband of his home village with a horizontal line gouged through it to symbolize his broken ties with the village. On his right ring finger was his Akatsuki ring, which bears the kanji for Vermilion (朱, shu). He also wore a necklace with three metal circles or rings on it.