Izaya Orihara (Durarara)
We only see him in one basic outfit throughout the show but it doesn't get much cooler when it comes to a guy's style than Izaya. It just looks so fresh and laid-back and the monochrome palette really suits his shady personality so who needs multiple outfits? Kudos to the people who did the character design for incorporating the minimalist trend into his look before it became a huge deal. Also check out the female version of Izaya. I'm definitely going to start wearing my parka with a dress now.
Amane Misa (Death Note)
Misa is not exactly what you would describe as a powerful female lead and she's not the most popular female character but she does know how to dress. Her style is feminine with plenty of goth elements incorporated that contrast with her sweet and naive personality but nonetheless if you want to look a bit more feminine while also maintaining an edgy vibe her style is great for inspiration.It is basically a softer, more "conservative" version of the goth lolita look that is so popular in Japan. Some elements are a bit outdated as the anime is pretty old(I think it came out in 2007) and her outfits can be more than a bit revealing but it is still a really distinctive look.