Data on the association of blood pressure (BP) phenotypes with office and out-of-office markers of vascular stiffness and pressure wave reflection are sparse. This study investigated office and 24-h measures of brachial BP, pulse wave velocity (PWV), and central augmentation index (AIx) across hypertension phenotypes among individuals not using BP-lowering medications [normotension (NT), white-coat hypertension (WH), masked hypertension (MH) and sustained hypertension (SH)] and those using BP-lowering medications [controlled hypertension (CH), white-coat uncontrolled hypertension (WUCH), masked uncontrolled hypertension (MUCH) and sustained uncontrolled hypertension (SUCH)]. We evaluated 454 untreated (age = 45 ± 15 years, 50% males) and 238 treated (age = 52 ± 15 years, 45% males) individuals who underwent office and 24-h brachial BP, PWV, and AIx measures using a Mobil-O-Graph PWA monitor. In the analysis adjusted for age and sex, WH had higher (p < 0.05) office PWV (7.53 ± 0.09 vs 6.89 ± 0.05), office AIx (27.9 ± 1.3 vs 23.8 ± 0.8), and daytime AIx (24.6 ± 0.7 vs 22.7 ± 0.4) compared with those of NT, while WUCH had higher (p < 0.05) office PWV (8.28 ± 0.11 vs 7.43 ± 0.08) and 24-h PWV (7.54 ± 0.09 vs 7.21 ± 0.07) than those of CH. MH had higher (p < 0.05) 24-h PWV (7.00 ± 0.09 vs 6.69 ± 0.04) and 24-h AIx (24.3 ± 0.9 vs 21.9 ± 0.4) than those of NT, whereas MUCH had higher (p < 0.05) 24-h PWV (7.64 ± 0.13 vs 7.21 ± 0.07) than that of CH. Lastly, SH or SUCH had significantly higher office and 24-h PWV and AIx than those of NT and CH, respectively. In conclusion, these results suggest that individuals with masked BP phenotypes are more predisposed to have adverse out-of-office vascular characteristics, while individuals with white-coat phenotypes have adverse office and out-of-office vascular characteristics compared with those of individuals with normal BP levels.