This study assessed test-retest reliability and relative validity of the Short Diet Questionnaire (SDQ) and usability of an online 24 h recall among 232 participants (62 years ± 9.1; 49.6% female) from the Canadian Longitudinal Study on Aging (CLSA). Participants were asked to complete four 24 h dietary recalls (24HRs) using the Automated Self-Administered 24-h Dietary Assessment Tool (ASA24-Canada-2014), two SDQ administrations (prior to recalls one and four), and the System Usability Scale (SUS) for ASA24. For the SDQ administrations, Intraclass Correlation Coefficients ranged from 0.49 to 0.57 for nutrients and 0.35 to 0.72 for food groups. Mean intakes estimated from the SDQ were lower compared than those from the 24HRs. For nutrients, correlation coefficients were highest for fiber, calcium, and vitamin D (45–64 years: 0.59, 0.50, 0.51; >65 years: 0.29, 0.38, 0.49, p < 0.01); Kappas ranged from 0.14 to 0.37 in those 45–64 years and 0.17 to 0.32 in participants >65 years. Among the 70% who completed all recalls independently, the SUS indicated poor usability, though the majority reported feeling confident using ASA24. Overall, the SDQ captures intake with varying test-retest reliability and accuracy by nutrient and age. Further research is needed to inform use of a more comprehensive dietary measure in the CLSA.