Tumors involving clavicle, ribs, and sternum are not very frequent, and yet they often pose significant diagnostic challenges. Even the benign lesions of the shoulder girdle and chest wall bones can show aggressive imaging features and appear destructive radiologically. A systemic imaging approach that includes plain radiograph, CT scan, MRI, and, when indicated, PET-CT scan is essential. Correlation with clinical and histopathological findings helps in the management of these patients. Clavicle is a modified long bone; however, it has pattern of neoplastic lesions like flat bones. Malignant tumors like Ewing’s sarcoma, chondrosarcoma, osteosarcoma, and multiple myeloma affect clavicle more commonly than benign lesions like osteoma, osteoid osteoma, osteoblastoma, and enchondroma. Primary tumors of ribs are rare; however, they are often seen due to the high number of the bones of the ribs and higher frequency of the chest radiographs obtained for various conditions showing incidental rib lesions. Tumor like lesions are more commonly seen in ribs compared to primary tumors of the ribs. Metastasis is one of the most common malignant tumors that affect ribs and sternum, while the most common primary neoplasm of sternum and chest wall is chondrosarcoma. Many infective and inflammatory conditions as well as benign changes like post-traumatic and stress-related changes can mimic tumors of ribs and sternum. Even post-sternotomy changes can resemble osteolytic or mixed tumor of the sternum.