Severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) virus was discovered in China in late 2019 and subsequently triggered a global pandemic. Dentists, like many other health professionals, are at an increased risk of contracting the virus as they work in close proximity to patients, especially when performing aerosol-generating procedures. Thus, in order for dentists to protect themselves and their patients, it is recommended that practitioners wear filtering facepiece 2 (FFP2) respirators. The prolonged use of these FFP2 respirators has been linked to several side effects. The aim of this paper is to assess the perceived experience associated with N95/FFP2 respirators based on the available literature and data collected through an online survey completed by Italian dental professionals. Articles were included up to May 2020 and literature searches were conducted through The National Library of Medicine, Cochrane Central Register of Controlled Trials, and Embase databases. The search terms included COVID-19, respirators, masks, and discomfort. An online survey was administered to 256 Italian dentists. The results from this survey were in agreement with the available literature. The findings concurred that the prolonged use of respirators was associated with headaches (47.5%), severe exertion and discomfort (50.8%), moderate concentration problems (54.3%), moderate breathing difficulties (63.5%), and consequently, an impaired work ability (85.5%). These findings were not influenced by the number of hours spent wearing the respirator. Despite several side effects, FFP2 respirators are fundamental in protecting dentists and their importance was acknowledged.