I think it is different to feel that looks are important/unimportant and simply feeling confident and comfortable regardless of the definition of that beauty or the importance placed upon it. Beauty is a fad, it changes. But your confidence shouldn't, IMO, based on it. I agree it shouldn't matter, and people shouldn't care, but that doesn't mean we shouldn't just be confident with what we have, regardless if it is "in" or not.
Not caring means something different to everyone, too. Does it mean don't dress nicely? Don't try to clean up? We shouldn't bother with makeup or getting our hair groomed? If it honestly doesn't matter....why bother?
After all, it should be my personality and qualifications that gets me a job, not a well cut suit. Unfortunately, it just isn't realistic.