I think in her head Anna sees herself as this cool girl and tries to give off a vibe as if she's in NY or LA or something. That's why often she goes for not-so-mainstream brands in the UK, spends a looooot of money on some simple pieces and pretends she's got a 'capsule wardrobe'.She has a great body so I don't know why she's lost her style.
I just think it is a bit try hard because honestly, she's just this nice girl in Brighton who really isn't that cool but that's okay. She should embrace it. I loved it when she would wear skinny jeans, ankle boots and some more form-fitting tops. She looked really good then and it complimented her figure perfectly.