I'm trying to figure out what it means to apply a linear transformation to a vector field geometrically. So I start with the easiest geometrically interesting transformation: a rotation.
Using StreamPlot in WolframAlpha I see that applying the transformation $T(x,y) = (-y,x) = \pmatrix{\cos(90^\circ) & -\sin(90^\circ) \\ \sin(90^\circ) & \cos(90^\circ)}\pmatrix{x \\ y}$ yields exactly what I'd expect: circular stream lines:
However when I try a different angle, say $\pi / 6$, then I have $T(x,y)=\left(\frac{\sqrt{3}}{2}x-\frac12 y, \frac12 x + \frac{\sqrt{3}}{2}y\right)$. But the picture no longer looks like circles, but spirals:
Clearly something's wrong with my interpretation here. Why do the stream lines look the way they do? How can I imagine linear transformations being applied to vector fields?


(I'll keep it simple, so this explanation sacrifices a lot of generality.)
There are two ways to apply a linear transformation to a vector field: multiplication and conjugation. What you've observed is the difference between the two.
Multiplying a vector field (on the left) rotates all the arrows in-place. If you start with a vector field that looks like circles, and you rotate all the arrows a bit, they no longer go in circles; they either spiral into or out of the origin. This is the relationship between your two versions of $T$; you can write $T_2 = RT_1$ for some rotation $R$.
It sounds like you expected the vector field to look the same, just rotated in space. That would indeed be the case if you had conjugated $T$ by a rotation, getting $T_3=RT_1R^{-1}$. In fact, since 2D rotations commute with each other, you would have $T_3=T_1$: the two vector fields would look exactly the same.