Image similarity has been extensively studied in computer vision. In recent years, machine-learned models have shown their ability to encode more semantics than traditional multivariate metrics. However, in labelling semantic similarity, assigning a numerical score to a pair of images is impractical, making the improvement and comparisons on the task difficult. In this work, we present a more intuitive approach to build and compare image similarity models based on labelled data in the form of A:R vs B:R, i.e., determining if an image A is closer to a reference image R than another image B. We address the challenges of sparse sampling in the image space (R, A, B) and biases in the models trained with context-based data by using an ensemble model. Our testing results show that the ensemble model constructed performs ~5% better than the best individual context-sensitive models. They also performed better than the models that were directly fine-tuned using mixed imagery data as well as existing deep embeddings, e.g., CLIP and DINO. This work demonstrates that context-based labelling and model training can be effective when an appropriate ensemble approach is used to alleviate the limitation due to sparse sampling.