Sometimes, one person or one unfortunate incident can ruin a fashion choice for everyone. For instance, November 22nd, 1963, was probably the nail in the coffin for the pink pillbox hat.
Also, no matter how much of a film comedy buff you are, you aren't going to wear a Hitler mustache and refer to it as an "Oliver Hardy mustache". "What? Why are you looking at me like that? I just enjoy Laurel and Hardy! What's wrong with that?"