This Ermenegildo Zegna suit in a windowpane plaid is a gutsy, rakish play. So embrace it. A proper English spread-collar shirt merits a wider knot (like a full Windsor) to fill that extra gap between the collar points. Who wouldn't give a promotion to the guy dressed like royalty?

Windowpane-plaid suit, $2,950, and sartorial dress shirt, $435, both by Ermenegildo Zegna; silk paisley tie by Z Zegna, $125