I think there's a greater underlying dichotomy here that's relevant to your tailor-made suit analogy: the people who love Perl tend to be the people who are building and maintaining mostly only their own tooling and (usually small) codebases, and the people who don't love Perl tend to be the ones that are responsible for maintaining large piles of other people's code.

A language that's "tailor-made" for the individual is fantastic when you only have to deal with your own code. You get to write stuff that makes sense to you. It doesn't matter if it's unconventional or doesn't make sense to anyone else -- it fits the way that your brain works.

But when cooperating on larger projects with lots of other people involved, this backfires remarkably. You now need to understand the way that half a dozen or more other brains work.

As software development has gradually shifted away from the published efforts of lone hackers and towards the collaborative efforts of teams of specialized people, Perl's "TMTOWTDI" approach has made it a far more expensive language to develop software in than all of the alternatives.