We will define what it means for $f:S\to S$, a homeomorphism, to be orientation preserving/reversing. You pick any point $p\in S$, since $S$ is a surface there is a homeomorphism $\mathbb{R}^2\to U$ where $U$ is an open subset of $S$ containing $p$ and the pre-image of $p$ is $(0,0)\in \mathbb{R}^2$. Likewise, there is another homeomorphism $V\to \mathbb{R}^2$ where $V$ is another open set of $f(p)\in S$ and this homeomorphism maps $f(p)\mapsto (0,0)$.
The composition will give you, $\mathbb{R}^2\setminus \{(0,0)\}\to \mathbb{R}^2\setminus\{(0,0)\}$. Now pick any loop. If this map changes the sign of the winding number then we say that $f:S\to S$ is orientation reversing.
Of course, you need to show that this definition is well-defined, regardless of the choices that you make, however, you assume that $S$ is orientable itself, and so the atlas can be chosen consistently to keep this definition well-defined.
There is another issue to address, that the definition does not depend on the initial point $p$ chosen. This comes down to the fact that $S$ is connected and so the orientation cannot suddenly change as you move through out the surface.