I have this ill posed question which has been bothering me for a while now.
Let $x,y$ be arbitrary vectors in $\mathbb{R}^2$.
Does there exists a non-trivial linear transform $T$ where $w = T(x)$ always lies in the lesser of the two regions* in between $x$ and $y$?
(Two regions: one is the one where $w$ lies as shown in the picture, the other is where its reflection lies)
Is there a generalization to $\mathbb{R}^n$?


Your question is completely unclear to me; two vectors do not partition the space into two regions, let alone into one that is less that the other (whatever that could mean).
But if you are looking for $f$ such that the angle between $f(v)$ and $f(w)$ is always (strictly) less than that between $v$ and $w$ then look no further; it does not exist. (If you allow equality of angles, then you can take the identity of a scalar multiplication; not really thrilling.)
This is simply because flat angles (as between $v$ and $-v$) are always preserved by a linear transformation. An even if you would exclude flat angles from your condition of decreasing angles, just divide a flat angle into a finite number of smaller angles; if they are all becoming smaller, then so is their sum, but this sum has to remain a flat angle.