If the classic mid-century inspired matching dress and tie colour is your ultimate accessory, ensure the event calls said formality. Weddings, formals, race days or special event cocktail parties are some of the few occasions in which complete matchy-matchy is perfectly acceptable. After all, at the right place and right time, it can be cute. A date consisting of just the two of you to do the groceries is not one of those occasions.
Stick by the golden rule: match to the occasion, and fear not the embarrassingly awkward and unnecessary formality.