I figured the hair in the first pic wasn't brushed or anything, yes.

Fine. Fine. The medium length/almost shoulder length hair looks good enough, then. :P
Better than the super duper short, in my singular opinion. But that's just one opinion to note and move on, of course.

I get why you keep saying "I can't do that!" and keep giving excuses for why things don't work because you try to be objective and not shy away from criticisms of yourself. You're your own worst critic, you know.

The last thing I want to say is, you are pretty enough that you can focus on the compliments instead of making sure you're being objective and telling people why you feel like you'd look worse other ways - or telling them why other ways wouldn't be worth it. So: you're attractive. Stop worrying.

As for the side of you that likes to argue and be critical, I'm bored so I can entertain that too :P
You really can't tan? Come one! Don't you know anything about cooking? If you throw a steak on an oven top, it'll turn brown on the outside almost immediately, but you have to keep cooking it for the inside to turn brown!

You can't just go outside, get burned, and then call the steak done! (Just use sunscreen, of course.)
Like I said: I'm not saying to get a tan anymore. Just saying... I'm a pale person who has said the same things before, except when I look at photos of me when I was young and played sports all day I always remember, "Oh, right... I did used to have a tan. Must have taken me like 7 years."

Everything is just an excuse :P
We all make excuses. I've done the same with tanning, and my hair. And I'm a dude! I used to have long hair and dreaded short hair (opposite of you), and now I wish I could literally burn all of my old photos where I had long hair because I finally feel handsome - and I just so happen to have short hair now that I have my looks "figured" out.

Honestly, there's no point to saying to try out new styles because you're young and you're going to try out new styles eventually - just like me and my short hair. But I The reason I'm using the tanning and hair examples as the crux of my argument for you giving excuses though is because maybe you'll realize that the rest of the reasons you give for why you can't try other styles or looks are all just as silly as saying you literally can't tan - because like 99% of people can tan and unless a doctor told you you can't I know you know you're just being silly :P

Now keep doing what you're doing and being silly and saying you can't tan or change your hair until you eventually change one of them and realize you like it, because that's also how like 99% of people seem to do things. hahaha