Capitalizing on the all-sky coverage of WISEand the 35% and 50% sky coverage from Sloan Digital Sky Survey and Pan-STARRS, respectively, we explore the efficacy of-, as a color diagnostic to identify obscured supermassive black hole accretion in wide-area X-ray surveys. We use the ∼16.5 deg 2 Stripe 82 X-ray survey data as a testbed to compare R W1 -with R−K, an oft-used obscured active galactic nucleus (AGN) selection criterion, and examine where different classes of objects lie in this parameter space. Most stars follow a well-defined path in R−K versus R W1space. We demonstrate that optically normal galaxies hosting X-ray AGNs at redshifts z 0.5 1 < < can be recovered with an R W1 4 -> colorcut, while they typically are not selected as AGNs based on their W W 1 2 -colors. Additionally, different observed X-ray luminosity bins favor different regions in R W1 -parameter space: moderate-luminosity AGNs > -erg s −1 ) have bluer colors; higher spectroscopic completeness of the Stripe 82X sample is needed to determine whether this is a selection effect or an intrinsic property. Finally, we parameterize X-ray obscuration of Stripe 82X AGNs by calculating their hardness ratios (HRs) and find no clear trends between HR and optical reddening. Our results will help inform best-effort practices in followingup obscured AGN candidates in current and future wide-area, shallow X-ray surveys, including the all-sky eROSITA mission.