The blazer's day off.

Why it works

Smart-casual office is the brief everyone overshoots. A waistcoat and a good loafer carry the authority a whole suit would, with one less layer to sit in through a 4pm that runs long. The Boss striped button-front holds at $45 in all three rails (a crisp poplin reads the same under a vest whatever it cost), which leaves the trouser and the tote to absorb the budget.