love the snark, but this is really very simple:
navy or charcoal suits: solids first, then stripes...leave out the POW and glenplaid
white or blue shirts: solids first, stripes later. contrast collars...fuck no, you're not gordon gekko
ties: muted, navys, burgundy, dark green, grey, etc
shoes: dark brown and black if you must. possibly walnut on a saturday when you're dragging your ass to work:
Nightlife: Pajamas...you think you're going out? ...