A tailored midi dress means the fit is considered through the shoulders and waist with seams that shape rather than just hang. Tailored construction in a midi dress reads as intentional and formally dressed. The hem should reach below the knee without dragging. Black is the correct choice and it makes the tailoring more visible. Look for dresses where the waist is defined and the bodice has some structure rather than flowing loosely. A simple neckline keeps the focus on the tailoring and proportion rather than any decorative element. These are the midi dresses that work because they are built specifically for occasions where you want to look polished and put together.