The COVID-19 lockdown and the consequent distance school learning made epochal changes in children’s lifestyles; however, little is known about the lockdown effects on school teacher habits. The aim of this observational study is to examine differences in the lifestyle of nursery (NS) and primary (PS) school teachers after one of the COVID-19 lockdowns and investigate the relationship between perceived physical/mental health and demographics, weight status and lifestyle determinants, such as adherence to the Mediterranean Diet (MD) and physical activity level (PAL). A total sample of 265 participants (49.22 ± 6.95 years) filled out an online information questionnaire and standardized questionnaires to collect data on the Physical Component Summary (PCS), Mental Component Summary (MCS), PAL and MD-adherence. A t-test or ANOVA analysis was used to assess differences between quantitative variables: Mann–Whitney U or Kruskal–Wallis tests for qualitative variables. Spearman’s correlations and multinomial logistic regression analyses were performed to identify categorical factors associated with classes of PCS and MCS. Teachers showed sufficient/high PAL, with a significantly higher level in the PS group (p < 0.05). This last showed a higher PCS score (p < 0.05). No differences between groups were found for MD-adherence, which was moderate/fair in both groups, and MCS, which was sufficient/good. Logistic regression showed that the only positive predictor of a high PCS was being physically active (OR 2.10, 95%CI 1.05–4.2, p < 0.05), while MCS was positively associated with normal weight status (OR 0.48, 95%CI 0.33–0.78, p = 0.020). This study highlights that PS teachers are more active than the NS group and perceive a higher physical health level. Mere predictors of physical and mental well-being are PA practice and being normal weight, respectively. This suggests that interventions to improve perceived health in this work category should be focused on the promotion of physical activity practice and on the maintenance of an optimal weight status.