For the girls you showed there's a lot of different lengths so I don't know what length you were thinking. Also have you thought about how you would style it like that everyday. That's the problem, it's actually a lot easier/less maintenance to look good with long hair because you don't need to wash and style it in the way you do short hair, every single morning lol. So you need to think about these things before you do it. It's a commitment lol.
You have a similar facial structure to me and I have been through all lengths from extremely short to extremely long. I would generally say it's fun to change up lengths and styles for a while, just to try it out, you are young you can experiment. But as someone with similar facial structure to you and also brunette, I can tell you that probably the best look is shoulder length or longer. But if you want to be out there and go for the chop do it! If you maintain it properly with natural hair masks and don't over kill with dying and styling then it will grow back considerably in a year.