Here$\let\leq\leqslant\let\geq\geqslant\newcommand\and{\text{ and }}$ is one way to see why the equality holds, but this approach does not involve the Möbius-function.
$\sum_{b\mid n}^{n\leq a} 1$ counts the number of multiples of $b$ that are less than or equal to $a$. Let's write and rewrite this property in a symbolic way:
$$n\leq a\and b\mid n\iff n\leq a\and n=kb\text{ for some }k\iff k\leq\frac ab\and n=kb\text{ for some }k.$$
So we're counting the number of integers $n$ for which $n=kb$ and $k\leq\frac ab$. Clearly, every such $n$ corresponds to a unique such $k$, so counting the number of $k$'s for which
$$k\leq\frac ab$$
is exactly the same question as counting the number of $n$ satisying the said condition.
There are exactly $\left\lfloor\frac ab\right\rfloor$ such $k$.