Suppose we have a linear map $T$ whose matrix is $A$ such that $$A: V \rightarrow V$$ where $A$ is the transition matrix from the basis $v_1,v_2,...,v_n$ to the basis $w_1,w_2,...,w_n$.
If the determinant of $A$ is positive, then the orientation of the basis $v_1,v_2,...,v_n$ if the same as $w_1,w_2,...,w_n$. If negative, then they have opposite orientations.
Can someone explain why this is? Why are two bases oriented the same if the transition matrix has a positive determinant? What does it mean for two bases to be of the same orientation?
It's basically the definition of ‘same orientation’ and ‘opposite orientation’. To change basis between two bases of same orientation (in $\mathbb{R}^n$), you need to perform a rotation (i.e. orthogonal matrix) and a scaling/shearing (i.e. positive-definite matrix). If, however, you want to change between two bases of different orientations, you have to perform a reflexion as well. Think of it like this: every basis that is oriented differently is just a basis oriented equally with two swapped basis vectors, just as every invertible matrix of negative determinant is just an invertible matrix of positive determinant with two rows swapped