Frequent droughts induced by climate warming have caused increasing impacts on the vegetation of the Loess Plateau (LP). However, the effects of drought on vegetation are highly dependent on when the drought occurs and how long it lasts during the growing season. Unfortunately, most of the existing drought indices ignore the differences in the drought effects on different vegetation growth stages. In this study, we first established a phenology-based vegetation condition index, namely weighted vegetation condition index (WVCI), which accounts for the differences in vegetation sensitivity to drought by assigning specific weights to different phenological stages of vegetation. Then, we used the WVCI to reveal the temporal and spatial variations in vegetative drought from 2001 to 2019 over the LP from the aspects of drought frequency, trend and relative deviation. The results showed that (1) the LP experienced frequent droughts during the study period, but mainly mild and moderate droughts. The drought frequencies decreased from southeast to northwest, and extreme droughts rarely occurred in mountainous areas and plains. (2) The droughts in most areas of the LP tended to ease, and only a few areas in the Hetao Plain, Ningxia Plain and Fenwei Plain showed an increasing trend of drought. (3) After 2012, the departure percentage of WVCI in most areas of the LP was positive, indicating above-average vegetation conditions. (4) Compared with the well-established vegetation condition index, the WVCI proved to have the ability to monitor and assess vegetative drought on an annual scale in the LP. As a result, our research could help develop and implement drought-resistance and disaster-prevention measures on the LP.