The flexible attachable tip is manufactured to repeatedly connect as well as disconnect to a body of a hearing assistance device. The flexible attachable tip is manufactured to have two or more offset layers of flexible earmolds. The tip has a dome-shaped earmold that is separated by an air gap from offset layers of inner earmolds. Each layer of ear mold has multiple bendable members with an air vent constructed into the bendable members for that earmold. Air space is formed in between each of the individual bendable members making up the flexible earmold for a given layer of the offset layers. The flexible earmolds including their bendable members bend to a deformed state in order to secure the hearing assistance device in position inside an ear canal, which prevents the device from falling out of an ear, while still providing both a sound path and an airflow path through the ear canal.