And then you have to consider what the outfits actually mean. You have to give the guy props, particularly PI Riddler:
He went around like this, in all seriousness, saying, ‘I am perfectly sane and you should hire me at an outrageous rate to solve mysteries for you’. That takes a huge amount of self-confidence to pull off. He went around dressed like a weirdo and demanded to be taken seriously, and by many people he was! That is hard to do. Even beyond that, he usually goes around wearing whatever combination of green or purple clothes. I have never seen a green suit in my life, yet even when he’s ~blending in~ he still walks around in a green suit. Why does no one wear a green suit? It’s weird! It’s confusing! It takes guts to wear one! All things that add to his personality.
Even Spandex Riddler falls under the same principle. Heroes wear spandex to show off what’s underneath. Villains such as Deathstroke and Deadshot do the same thing. And yet the Riddler to this day on occasion still walks around in spandex not to up play his ridiculousness (not completely, at least), but because he has the presence to pull it off. He’s got nothing underneath that spandex that intimidates anyone. (please take that sentence at face value) He wears it because he wants to, demands to be taken seriously and very often is. The best spandex Riddlers are the ones that don’t have significant muscle mass because with an outfit like that, it takes a ton of self-confidence to walk around while your uniform says, ‘I’m not that impressive in spandex, but I like it anyway so here I am’. It’s weird, but he’s not immediately discredited because of it.
Riddler’s outrageousness is a byproduct of his self-confidence; he only scales it back when he’s upset with himself. He likes being noticed and he wants there to be something to notice. And that’s why he can be taken seriously in just about everything except for… most of the outfits in that one movie. Because he’s so brazenly taking himself seriously.
New 52 Riddler reminds me of a line from Batman Beyond Return of the Joker: “So you fell into a tank of acid, got your skin bleached, and decided to become a supervillain. What, you couldn’t get work as a rodeo clown?” Slightly different scenario, and yet similar. He doesn’t feel like he’s taking himself seriously. He feels like he’s saying, “I’m doing this because I’m bored,” which he was. But the difference between him and other Riddlers is that the doing excited him, where New 52 Riddler actually says he’s not happy doing it.