There are many synonyms for the phrase "with head held high." One of the most common synonyms is "proudly." Other possible synonyms include confidently, resolutely, unashamedly, unabashedly, boldly, gallantly, and unyieldingly. These synonyms all convey a sense of strength and resolve that comes from holding one's head up high. Whether it's in triumph or in the face of adversity, holding one's head up high is a sign of courage and determination. Those who can do so are often looked up to as examples of true leadership, and their strength in the face of adversity can be an inspiration to us all.