The aim is to analyze the bra design features and fit problems of older women and to design solutions to improve bra fit and design for older women. Twenty-six participants aged 62 ± 4 years participated in bra fitting experiments with eight commercial senior bras featuring different design features. The bra design features were firstly quantified into 19 parameters including dimensions and/or curvatures, material properties, bra tension and elongation. The associations between bra design features and related problems were then systematically addressed. The most common fit problem was bulging, which was affected by underarm height (r = 0.23, p < 0.01), underband elongation (r = –0.25, p < 0.01), rigidity of wing fabric (r = 0.30, p < 0.01), rigidity of top of the elastic underband (r = 0.32, p < 0.01), rigidity of bottom elastic band (r = 0.32, p < 0.01), and tension of the underband (r = 0.23, p < 0.01). Except for neckline length, other measurements were also found to be related with bra fit problems. The well-fitting bras for older women have wide straps, large width at the front of strap, sufficient vertical cup length, increased gore height and underarm height, fabric straps on the back, and an underband with high rigidity. The reasons are discussed, and new design solutions are given. The design recommendations formulated in this study can advance the design and development processes of bras for older women.