Sasuke Uchiha is the principal frenemy/antagonist of Naruto and Naruto: Shippuden. He started off as Naruto's teammate and friend but eventually left to train under Orochimaru, a man who had already tried several times to destroy the Village Hidden in the Leaves. Sasuke stayed with Orochimaru during the time-skip between Naruto and Naruto: Shippuden. He eventually left Orochimaru and, after a few revelations and disasters, joined up with Naruto to fight Obito, Madara, and Kaguya. Sasuke and Naruto had one final showdown at the end of Shippuden, but Sasuke still went onto have a child with Sakura and become friendly with the Leaf Village again by the time of Boruto.
Sasuke has gone through more costume changes than anyone else in the show and certainly more than Naruto himself. Today, we are going to rank those costumes from least to most fashionable.
10 Shippuden 1
This is easily the worst of Sasuke's outfits. It opens farther down than any other, and it's just an odd twist of Orochimaru and Kimmimaro's costumes. It feels like Sasuke's "Hugh Hefner" costume. It doesn't feel like the uniform of a deadly shinobi warrior; it feels like the costume of someone looking to get lucky with any kunoichi that crosses his path. In short, it's not a very good outfit and easily earns its place at the bottom of this list.
9 Baby Sasuke
It feels a bit odd to judge the fashion choices of Sasuke from when he was but a young child and his brother slaughtered his entire family before his very eyes. That said, it is a different color and aesthetic combination from what Sasuke wore at the other points in his life. It's a fairly muted black-on-gray and seems to foreshadow Sasuke's disposition for the rest of his life.
8 Shippuden 4
This was the final costume that Sasuke wore during the Naruto: Shippuden series, and it is a vast improvement over his original Shippuden costume.
There is more of a color theme, the collar looks cool, and he doesn't look like he's in the process of stripping down in a manner that would impede his fighting. It's also a decent color contrast to Naruto's own orange jumpsuit.
7 Naruto: The Last 1
Naruto: The Last Movie saw Sasuke Uchiha donning a new look -- one more reminiscent of a wandering samurai ronin than a shinobi of Konohagakure. He wore a sand-brown poncho over a black tunic and torn black pants. He also wore a large headband that restricted his wild hair. It was a great look and matches the kind of person Sasuke had become. He found some loyalty to the Hidden Leaf Village, but he couldn't quite call it home.
6 Naruto: The Last 2
This was the second costume that Sasuke showed off during Naruto: The Last. It foreshadows what his Boruto uniform would look like, but it's more muted and almost completely black. That said, it still looks great and suits adult Sasuke very well.
5 Original Series 1
Of course, we have a lot of love for the original Sasuke outfit from Naruto. The blue collared shirt over plaid shorts gave the character an iconic look. He would later add a kunai holster to the shorts and forearm warmers. Those were actually a nice touch too, and this will forever be the look that comes to mind first when someone thinks of Sasuke Uchiha.
4 Shippuden 2
This is Sasuke's second costume from Naruto: Shippuden. He dons it after leaving Orochimaru and setting out to finally get his revenge on Itachi for slaughtering the Uchiha Clan.
It's famously also when he debuted his famous Jutsu, Kirin. It's a purple vest over bandages and the purple waist-cloak and tie that are associated with Orochimaru's followers. It just looks cool, flamboyant, and suits Sasuke well. That said, some of the appeal might just come from Kirin.
3 Boruto
Sasuke's Boruto costume is an instant classic. He's finally tamed that wild hair of his, has donned a dark blue cloak over a light-blue tunic and dark blue pants. It looks cool, it's somewhat reminiscent of his original look from Naruto, and he just looks like an all-around badass. It's a great look for the grumpy shinobi.
2 Original Series 2
The black onesie was also an iconic look for Sasuke Uchiha. It had a dramatic debut during Sasuke's Chunin Exam showdown with Gaara of the Sand. It's also when Sasuke first unveiled his Chidori, which was taught to him by Kakashi. He kept the look for his first showdown with his brother, Itachi, when the Akatsuki first visited the Leaf Village. Ultimately, it works because the basic look is simple but has some flavor added by the bandages and accessories on his arms. Also, it was the premiere of the romper, which has only gotten more popular since then.
1 Shippuden 3
Sasuke's best costume was, ironically, just him apeing his brother's Akatsuki look. Sasuke's "Taka" outfit came about when he first brushed up against the Akatsuki and began hunting Jinchuuriki on Tobi's behalf. He still wears the Orichimaru waist-covering and rope underneath it, and his collar sticks out from the cloak. So, there are still little touches that differentiate it from the regular Akatsuki look. It's a great aesthetic for Sasuke and his associates, and it earns its place at the top of this list.