Phenotyping in the field is an essential step in the phenotyping chain. Phenotyping begins in the well-defined, controlled conditions in laboratories and greenhouses and extends to heterogeneous, fluctuating environments in the field. Field measurements represent a significant reference point for the relevance of the laboratory and greenhouse approaches and an important source of information on potential mechanisms and constraints for plant performance tested at controlled conditions. In this paper, we present a range of methods deployed within the German Plant Phenotyping Network (DPPN, www.dppn.de), focusing on plant architecture, photosynthesis, and water relations. Specialized field platforms (a) test innovative phenotyping technologies; (b) provide access to semi-controlled field installations to support breeding approaches for future CO2–concentrations (breed-FACE); and (c) study the translation of phenotypic properties from controlled environments to stands in the field. In this paper, we report that stereo imaging allows the quantification of canopy structure; active thermography estimates leaf water content and provides information on transpiration conditions: sun induced (SIF) and light-induced fluorescence transient (LIFT) techniques allow us to estimate remotely photosynthesis at canopy and leaf-to-plant level, respectively. Regarding photosynthesis, because the Fluorescence Explorer was recently selected, SIF will be measured by the next European Space Agency satellite Earth Explorer mission. All methods will be tested further and incorporated into (semi-)automated systems of sensors positioned in the field, introducing a promising portfolio to measure plant traits in field phenotyping and to enhance our understanding of relevant traits under natural conditions now and in the future.