A toy barber shop assembly allows a user to imitate cutting and styling hair within the setting of a simulated barber shop environment. The assembly includes a playhouse having a top wall, a bottom wall and a perimeter wall coupled to and extending between the top wall and the bottom wall. Each of the top wall, the bottom wall and the perimeter wall define an interior of the playhouse. A chair and at least one hairstyling implement are provided and are sized for positioning within the interior of the playhouse.