At variance with the long established paradigm that retinal arteriolar narrowing trails hypertension, several longitudinal studies, all based on conventional blood pressure (CBP) measurement, proposed that retinal arteriolar narrowing indicates heightened microvascular resistance and precedes hypertension. In 783 randomly recruited Flemish (mean age, 38.2 years; 51.3% women), we investigated to what extent CBP and daytime (10 am to 8 pm ) ambulatory blood pressure (ABP) measured at baseline (1989–2008) predicted the central retinal arteriolar equivalent (CRAE) in retinal photographs obtained at follow-up (2008–2015). Systolic/diastolic hypertension thresholds were 140/90 mm Hg for CBP and 135/85 mm Hg for ABP. In multivariable-adjusted models including both baseline CBP and ABP, CRAE after 10.3 years (median) of follow-up was unrelated to CBP ( P ≥0.14), whereas ABP predicted CRAE narrowing ( P ≤0.011). Per 1-SD increment in systolic/diastolic blood pressure, the association sizes were −0.95 µm (95% confidence interval, −2.20 to 0.30)/−0.75 µm (−1.93 to 0.42) for CBP and −1.76 µm (−2.95 to −0.58)/−1.48 µm (−2.61 to −0.34) for ABP. Patients with ambulatory hypertension at baseline (17.0%) had smaller CRAE (146.5 versus 152.6 µm; P <0.001) at follow-up. CRAE was not different ( P ≥0.31) between true normotension (normal CBP and ABP; prevalence, 77.6%) and white-coat hypertension (elevated CBP and normal ABP, 5.4%) and between masked hypertension (normal CBP and elevated ABP, 10.2%) and hypertension (elevated CBP and ABP, 6.8%). In conclusion, the paradigm that retinal arteriolar narrowing precedes hypertension can be explained by the limitations of CBP measurement, including nonidentification of masked and white-coat hypertension.