In two's complement, we deal with signed numbers by checking the leftmost bit. If this leftmost bit is a $0$, then it's positive, so we proceed like we do with unsigned numbers. Otherwise, if the leftmost bit is a $1$, then it's negative, so we have to do the "reverse the bits then add one" trick that you did when you converted $-10_{10}$ to binary. In general:
$$
-x = \overline x + 1 \iff x = -(\overline x + 1)
$$
Hence, since $1111~1111$ starts with a $1$ and we are dealing with two's complement, we have:
\begin{align*}
(1111~1111)_2
&= -((\overline{1111~1111})_2 + 1) \\
&= -((0000~0000)_2 + 1) \\
&= -((0000~0001)_2) \\
&= -1_{10}
\end{align*}