Powered Assistive Devices (PADs) have been proposed to enable repetitive, user-oriented gait rehabilitation. They may include torque controllers that typically require reference joint torque trajectories to determine the most suitable level of assistance. However, a robust approach able to automatically estimate user-oriented reference joint torque trajectories, namely ankle torque, while considering the effects of varying walking speed, body mass, and height on the gait dynamics, is needed. This study evaluates the accuracy and generalization ability of two Deep Learning (DL) regressors (Long-Short Term Memory and Convolutional Neural Network (CNN)) to generate user-oriented reference ankle torque trajectories by innovatively customizing them according to the walking speed (ranging from 1.0 to 4.0 km/h) and users’ body height and mass (ranging from 1.51 to 1.83 m and 52.0 to 83.7 kg, respectively). Furthermore, this study hypothesizes that DL regressors can estimate joint torque without resourcing electromyography signals. CNN was the most robust algorithm (Normalized Root Mean Square Error: 0.70 ± 0.06; Spearman Correlation: 0.89 ± 0.03; Coefficient of Determination: 0.91 ± 0.03). No statistically significant differences were found in CNN accuracy (p-value > 0.05) whether electromyography signals are included as inputs or not, enabling a less obtrusive and accurate setup for torque estimation.