If a middle aged guy is too into fashion he comes across as a little weird and self absorbed. But if a guy is making six figures and dresses like a slob, or is wearing clothes/styles from 10+ years ago, then I think most agree he needs to take a little more pride in his appearance.

Its funny because I work with an executive who is over the top with his fancy three piece suits, Trump shirts, and cuff links while the rest of us come to work in business casual. He comes across as very unrelatable to most of the organization. Meanwhile, another high level leader seems to wear the same combinations of dress shirts and slacks that he has owned since 1995, despite making well over $200k/yr. There's a happy medium where most men should live in between these two fashion extremes.