An earphone having an earphone housing including a tip portion dimensioned to be inserted into an ear canal of a wearer, a body portion extending outward from the tip portion, and a tube portion extending from the body portion. The body portion has a face portion that faces a pinna region of the ear when the tip portion is inserted into the ear canal. A primary output opening, that outputs sound from a driver in the housing to the ear canal, is formed in the tip portion. A secondary output opening, that outputs air from the ear canal to the surrounding environment, is formed in the face portion. The primary output opening and the secondary output opening are horizontally aligned when the tube portion is positioned vertically downward and an angle formed between the primary output opening, the tube portion and the secondary output opening is less than 90 degrees.