This paper proposes an introspective deep metric learning (IDML) framework for uncertainty-aware comparisons of images. Conventional deep metric learning methods focus on learning a discriminative embedding to describe the semantic features of images, which ignore the existence of uncertainty in each image resulting from noise or semantic ambiguity. Training without awareness of these uncertainties causes the model to overfit the annotated labels during training and produce overconfident judgments during inference. Motivated by this, we argue that a good similarity model should consider the semantic discrepancies with awareness of the uncertainty to better deal with ambiguous images for more robust training. To achieve this, we propose to represent an image using not only a semantic embedding but also an accompanying uncertainty embedding, which describes the semantic characteristics and ambiguity of an image, respectively. We further propose an introspective similarity metric to make similarity judgments between images considering both their semantic differences and ambiguities. The gradient analysis of the proposed metric shows that it enables the model to learn at an adaptive and slower pace to deal with the uncertainty during training. Our framework attains state-of-the-art performance on the widely used CUB-200-2011, Cars196, and Stanford Online Products datasets for image retrieval. We further evaluate our framework for image classification on the ImageNet-1 K, CIFAR-10, and CIFAR-100 datasets, which shows that equipping existing data mixing methods with the proposed introspective metric consistently achieves better results (e.g., +0.44% for CutMix on ImageNet-1 K).