The aim of this study was to evaluate whether knowledge on concussions and self-reported risk-taking and sensation-seeking behavior are associated with helmet wear amongst certified Canadian ski and snowboard instructors. A total of 612 participants completed an online cross-sectional survey. Participants were asked about helmet use (answer options: always; most of the time; sometimes; rarely; never) and knowledge on concussion. Risk-taking behavior was self-reported (answer options: more cautious vs. more risky), and they completed the Sensation Seeking Scale Form V. Demographics (sex, age, education, nationality), certified winter sport (skiing and/or snowboarding), level of certification (4 levels, from beginner to expert), years of experience, average skiing time per season, and history of concussion were also recorded. Self-assessment of risk-taking was significantly associated with helmet wear (p = .04) but was not included in the multivariate model, which included only the variables level of p < .01. The final prediction model shows that self-assessment of sensation-seeking behavior (OR = 1.12; 95% confidence interval [CI: 1.05, 1.20]), certification level (OR = 5.75; 95% CI [1.85, 17.88]), and sex (OR = .22; 95% CI [.06, .76]) were significantly associated with helmet wear. Thus, a smaller proportion of men with a certification level of 3 (intermediate to expert level) who reported more sensation-seeking behaviors are wearing a helmet compared with others. In contrast, knowledge on concussion was not associated with the frequency of wearing a helmet. These findings may help in the development of prevention campaigns that focus on the main factors playing a role in helmet wear to more effectively convince nonwearers to adopt the safest practice.