There are several ways to understand this result. One is to think how $I(x,y)$ is defined. It's the signal your instrument gives you at point $y$ when your source is a delta function (that is, a point source) at point x. In mathspeak, $O_\delta(y) = \int \delta(x) I(x,y) \mathrm{d}x$.
If your source is composed of many different points, you need to sum over all those, so you have $O(y) = \int T(x) I(x,y) \mathrm{d}x$. Notice that $I$ is Green's function for your system (you might have studied it at some point). Now, in many cases $I$ depends on $x$ and $y$ only through the difference, so you get the convolution. This last step depends on your instrument, but I'm fairly certain that it's the case for telescopes with good lenses/mirrors in the paraxial approximation.
Another way to understand this result is to think about the Fourier transform. For simplicity's sake, I won't be absolutely rigorous here.
Light at the star has an amplitude profile given by $T(x)$, and when it reaches the objective of your telescope it has diffracted, so you have its Fourier transform ($\mathcal{F}[T]$). The objective acts as a filter that lets some of this light through, and has a transmission profile $\mathcal{F}[I]$, so light just after the objective is the product of both functions: $\mathcal{F}[T]\,\mathcal{F}[I]$.
Finally, the image formed at the focal plane of the objective is the inverse transform of that product: $O(y)=\mathcal{F}^{-1}\{\mathcal{F}[T]\,\mathcal{F}[I]\}$
Using the convolution theorem, $O(y)=T\otimes I$