Honestly, is there any way these people would be cool in 2023?

Sure. They'd probably have different haircuts and different clothes, but great talent is timeless.

Yes. They look like they’d be hanging with Rex OrangeCounty or something.

They are

Do people really judge music based entirely on how the artists look?

Well, fashion's cycled around again and today they'd be wearing the modern style anyway, so don't see why not :p

I'm literally seeing people unironically wearing flares these days where I am. They'd fit right in, depending on the crowd.