Deep learning and convolutional neural networks allow achieving impressive performance in computer vision tasks, such as object detection and semantic segmentation (SS). However, recent studies have shown evident weaknesses of such models against adversarial perturbations. In a real-world scenario instead, like autonomous driving, more attention should be devoted to real-world adversarial examples (RWAEs), which are physical objects (e.g., billboards and printable patches) optimized to be adversarial to the entire perception pipeline. This paper presents an in-depth evaluation of the robustness of popular SS models by testing the effects of both digital and real-world adversarial patches. These patches are crafted with powerful attacks enriched with a novel loss function. Firstly, an investigation on the Cityscapes dataset is conducted by extending the Expectation Over Transformation (EOT) paradigm to cope with SS. Then, a novel attack optimization, called scene-specific attack, is proposed. Such an attack leverages the CARLA driving simulator to improve the transferability of the proposed EOT-based attack to a real 3D environment. Finally, a printed physical billboard containing an adversarial patch was tested in an outdoor driving scenario to assess the feasibility of the studied attacks in the real world. Exhaustive experiments revealed that the proposed attack formulations outperform previous work to craft both digital and real-world adversarial patches for SS. At the same time, the experimental results showed how these attacks are notably less effective in the real world, hence questioning the practical relevance of adversarial attacks to SS models for autonomous/assisted driving.