Talk to your tailor. Have him nip the waist, take in the sleeves and convert non-working buttons into functional ones.

Finish the look. Add a simple, pressed white pocket square. $25 for seven, at Brooks Brothers.

Walk tall. You're in a suit, damn it.

A black suit and a tan suit, eh? Those are great additions to have, but the two staples of a man's sartorial arsenal are exactly what you're looking for. We'd suggest starting with a classic two-button suit in a medium charcoal shade. It's obviously dressy, but has a casual ease—especially when paired with a knit tie and some suede shoes. With a narrow notch lapel and snug shoulders, this year-round wool suit is slimming without being a 'skinny suit.'