Recreational music exposure is a potential risk factor for noise-induced hearing loss (NIHL). Augmented hearing protectors have been designed with modified attenuation characteristics to combine hearing protection and listening comfort. However, to date, only a few independent studies have assessed the performance of those augmented protectors in realistic exposure conditions. This study compares the listening experience and temporary effects on cochlear status with different types of earplugs after exposure to contemporary club music. Five different types of commercially available hearing protectors were worn, all commonly used during leisure-time music exposure. Four of them were augmented premolded earplugs and the fifth type was an inexpensive, standard earplug frequently distributed for free at music events. During five different test sessions of 30 min each, participants not professionally involved in music wore one particular type of protector. Contemporary club music was played at sound pressure levels (SPLs) representative of concerts and bars. After each listening session, a questionnaire on sound quality and general appreciation was completed. In addition, otoacoustic emissions (OAEs) were measured directly before and after music exposure. The reported appreciation clearly differed depending on the addressed characteristics and the specific earplug type. In this test group, the reported appreciation mainly depended on comfort and looks, while differences in sound quality were less noticeable. The changes in OAE amplitude before and after noise exposure were small in terms of clinical standards. Nevertheless, the observed temporary shifts differed systematically for the different types of hearing protectors, with two types of musician earplug showing a more systematic decline than the others. Further research with respect to actual use and achieved protection for real, unsupervised music exposure is warranted.