You're too hip to own a shirt that dark, or to wear it with a tie.
I believe sedate patterned silk hanks exist, and striped suits are either quietly desperate, subtle dignified, or ludicrously overconfident. A DB with wide lapels falls into the third category.
Pleated pants sit wherever the rise has them sit. Same as flat-fronts. Not a lot of low-to-mid rise pleats out there, though.
RJE, that's utterly killer.