EDIT: I rephrased the claim for clarity.
Let $k$ be a field (that we may assume to be algebraically closed, but I don't think it is necessary). Let $n\geq 1$ and $T$ denote the subgroup of $GL_n$ consisting of invertible upper triangular matrices.
Let $1\leq r \leq n$ and consider a sequence $a_1,\ldots,a_r$ of positive numbers such that $a_1+\ldots+a_r=n$. Consider the subgroup $P_{(a_1,\ldots,a_r)}$ of $GL_n$ consisting exactly of all matrices $M$ of the form $$M = \begin{bmatrix} M_1 & * & \dots & * \\ 0 & M_2 & \ddots & \vdots \\ \vdots & \ddots & \ddots & * \\ 0 & \dots & 0 & M_r \end{bmatrix}$$
with $M_i\in GL_{a_i}(k)$ for all $i$, and the $*$'s being any elements of $k$ (or rather, any matrices with coefficients in $k$ and of appropriate dimensions). In other words, $P_{(a_1,\ldots,a_r)}$ consists of all invertible upper-triangular by blocks matrices with diagonal blocks being squares of dimensions $a_1,\ldots,a_r$. The claim I am considering is the following:
Any subgroup $P$ of $GL_n$ containing $T$ must have the form $P=P_{(a_1,\ldots,a_r)}$ for some $r$ and $a_1,\ldots,a_r$.
I suspect that this result may be true, however I can't find a way to prove it. In particular, given a group $P$ containing $T$, I have trouble seeing how I could characterize $r$ and the (ordered !) sequence $a_1,\ldots,a_r$ solely in terms of $P$.
The motivation behind this lies in the theory of algebraic groups. We know that $T$ is a connected closed solvable subgroup of $GL_n$. With the above result, I could deduce that $T$ is maximal with respect to such properties, because all subgroups described above with $r<n$ are unsolvable.