Where is the Line?

So lately I have noticed a lot of outfits being posted by fashionista's, (gosh I hate that word), are getting a bit close to weird for my liking. So where do we draw the line? Or is it a matter of it being in style to push boundaries right now?

Stockholm Streetstyle

LookBook

The Sartorialist

Melbourne Street Fashion

What I hate most is the ability of these outfits to make my, what I always saw as classic, dress sense, feel boring. I start to doubt myself which is not something I often do and certainly don't like doing it, but if I were to slip on any elements of the above outfits, it would be down-right not me. At all.

So girls, (& guys?), I ask you;
Where do you draw the line between fashion and just plain weird outfit?
Is there no line due to expression of yourself through what you choose to wear?

I think expression is important, but does that make the above outfits photographed for their excellent use of clothing to express, or because the clothing is stylish? Or is it just stylish to express through clothing?

Does style not come into it at all, is it just fashion?

Circle talking,
Nat x