This study was aimed at comparing in-field parameters and remote sensing NDVI (normalized difference vegetation index) by both satellite (SAT) and unmanned aerial vehicle (UAV) for the assessment of early nitrogen (N) status and prediction of yield in winter wheat (Triticum aestivum L.). Six increasing N rates, i.e., 0, 40, 80, 120, 160, 200 kg N ha−1 were applied, half at tillering and half at shooting. Thus, when the crop N status was monitored between the two N applications, consecutive N treatments differentiated from each other by just 20 kg N ha−1. The following in-field and remote sensed parameters were compared as indicators of crop vegetative and N status: plant N% (w:w) concentration; crop N uptake (Nupt); ratio between transmitted and incident photosynthetically active radiation (PARt/PARi); leaf SPAD values, an indirect index for chlorophyll content; SAT and UAV derived NDVI. As reliable indicators of wheat N availability, in-field parameters were ranked as follows: PARt/PARi ≅ Nupt > SPAD ≅ N%. The PARt/PARi, Nupt and SPAD resulted quite strongly correlated to each other. At all crop stages, the NDVI was strongly correlated with PARt/PARi and Nupt. It is of relevance that NDVI correlated quite strongly to in-field parameters and grain yield at shooting, i.e., before the second N application, when the N rate can still be adjusted. The SAT and UAV NDVIs were strongly correlated to each other, which means they can be used alternatively depending on the context.