The aims of this study were to: (1) compare actigraphy (ACTICAL) and a commercially available sleep wearable (i.e., WHOOP) under two functionalities (i.e., sleep auto-detection (WHOOP-AUTO) and manual adjustment of sleep (WHOOP-MANUAL)) for two-stage categorisation of sleep (sleep or wake) against polysomnography, and; (2) compare WHOOP-AUTO and WHOOP-MANUAL for four-stage categorisation of sleep (wake, light sleep, slow wave sleep (SWS), or rapid eye movement sleep (REM)) against polysomnography. Six healthy adults (male: n = 3; female: n = 3; age: 23.0 ± 2.2 yr) participated in the nine-night protocol. Fifty-four sleeps assessed by ACTICAL, WHOOP-AUTO and WHOOP-MANUAL were compared to polysomnography using difference testing, Bland–Altman comparisons, and 30-s epoch-by-epoch comparisons. Compared to polysomnography, ACTICAL overestimated total sleep time (37.6 min) and underestimated wake (−37.6 min); WHOOP-AUTO underestimated SWS (−15.5 min); and WHOOP-MANUAL underestimated wake (−16.7 min). For ACTICAL, sensitivity for sleep, specificity for wake and overall agreement were 98%, 60% and 89%, respectively. For WHOOP-AUTO, sensitivity for sleep, wake, and agreement for two-stage and four-stage categorisation of sleep were 90%, 60%, 86% and 63%, respectively. For WHOOP-MANUAL, sensitivity for sleep, wake, and agreement for two-stage and four-stage categorisation of sleep were 97%, 45%, 90% and 62%, respectively. WHOOP-AUTO and WHOOP-MANUAL have a similar sensitivity and specificity to actigraphy for two-stage categorisation of sleep and can be used as a practical alternative to polysomnography for two-stage categorisation of sleep and four-stage categorisation of sleep.