Your condition on $X$ is that it has a kernel, and that by itself does not mean that
$X \wedge X$ doesn't have to vanish.  For instance in five dimensions, you could have 
$$X = \begin{pmatrix} 0 & 1 & 0 & 0 & 0 \\\\ -1 & 0 & 0 & 0 & 0 \\\\ 0 & 0 & 0 & 1 & 0 \\\\ 0 & 0 & -1 & 0 & 0 \\\\ 0 & 0 & 0 & 0 & 0 \end{pmatrix}.$$
Then letting $t = (0,0,0,0,1)$, your condition is satisfied, but $X \wedge X$ is not zero.

However, it is true in $2n$ dimensions that a non-zero $t$ exists if and only if $X^{\wedge 2n} = 0$.  That's because $X^{\wedge 2n}$ is proportional to the [Pfaffian][1] of $X$, which is a certain square root of the determinant of $X$.

  [1]: http://en.wikipedia.org/wiki/Pfaffian