Osteoporosis results in reduced bone strength and an elevated risk of fractures. Both overweight and underweight have been associated with osteoporosis; however, few studies have examined associations between osteoporosis and indices related to obesity. Therefore, the aim of this study was to investigate the associations of obesity-related indices, including body mass index (BMI), waist–hip ratio (WHR), waist-to-height ratio (WHtR), body roundness index (BRI), body adiposity index (BAI), abdominal volume index (AVI), lipid accumulation product (LAP), and visceral adiposity index (VAI), with baseline and change in calcaneus ultrasound T-score between baseline and follow-up (ΔT-score). T-score was measured using ultrasound. A total of 26,983 subjects were enrolled (mean age 51.2 ± 10.4 years). Multivariable analysis showed significant associations between low BMI (per 1 kg/m2; β, 0.065), WHR (per 1%; β, 0.012), WHtR (per 1%; β, 0.024), BRI (per 1; β, 0.079), BAI (per 1; β, 0.032), AVI (per 1; β, 0.049), and LAP (per 1; β, 0.005) with low baseline T-scores (all p < 0.001). Furthermore, there were significant associations between low BMI (per 1 kg/m2; β, 0.005; p = 0.036), BAI (per 1; β, 0.010; p < 0.001), and VAI (per 1; β, 0.017; p = 0.002) with low ΔT-scores. A low baseline T-score was significantly associated with low values of LAP, AVI, BAI, BMI, BRI, WHR, and WHtR but not VAI. In addition, low BMI, BAI, and VAI were significantly associated with low ΔT-scores, representing a rapidly decreasing T-score. Consequently, avoiding being underweight may help prevent osteoporosis in the Taiwanese population.