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Background/Objectives: This study examines the factors associated with U.S. adolescents’ obesity and overweight status. Methods: Using a multivariable logistic regression, we analyzed the data from the 2021 Youth Risk Behavior Surveillance System (YRBSS), comprising 17,232 students. Results: The odds of being obese or overweight were significantly higher (p ≤ 0.05) for the participants who perceived themselves as slightly overweight (AOR, 13.31; 95% CI [11.83, 14.97]) or very overweight (AOR, 39.29; 95% CI [30.12, 51.25]) compared to those who perceived their weight as about right. The participants with significantly higher odds included those aged 14 years (AOR, 2.53) compared to those aged 13 years or younger; male students (AOR, 1.63) compared to female students; and American Indian/Alaska Native and Native Hawaiian/Other Pacific Islander students (AOR, 2.11), Black or African American students (AOR, 2.63), Hispanic/Latino students (AOR, 1.54), and students of multiple races (AOR, 1.56), compared to White students. The odds were also significantly higher for the participants who did not eat breakfast on all seven days of a week (AOR, 1.21) and for the students who did not report their mental health status (AOR, 2.07) compared to those who reported their mental health as mostly or always not good. Conclusions: These findings suggest schools are uniquely positioned to implement strategies for healthier behaviors designed and implemented with a focus on health equity.