This study presents a new interpretation of symbols of the bride-maiden, already known in the Eastern Slavic, specifically Don Cossack tradition. It is based on findings of ethnographic expeditions of the 1980s–2000s to areas where Don Cossacks are concentrated, and on 19th-century periodicals published in the Don Region. To interpret the essence and meaning of bridal symbols, ritual practices and folklore texts are integrated, viewing both in the context of two principal passages that the bride undergoes during the wedding: 1) transition from the state of maidenhood to that of a married woman; and 2) transition from one family clan to another. Both transitions are related to the ideas of “beauty” (krasota), supposed to be lost during the ceremony, and “lot” (dolya)—part of the life force and benefits allotted to the bride from her family/clan during the rite and added to the common lot of her new family. Material embodiments of “beauty” (the braid, ribbon, and wreath) can be interpreted as symbols of freedom and virginity. These qualities are lost during the rite, whereas their material symbols are either destroyed or passed on to others. Symbols such as a small tree and twig (referring to the folkloric image of the “garden”) can be related to the idea of “lot”, and rituals in which they feature can be interpreted as a gradual disruption of the braid’s ties with her family clan, deprivation of her familial “lot” (symbolic death), followed by rebirth manifested in the acquisition of a new “lot”—that of a married woman in a new family clan. Existing classifications of bridal symbols are revised, while new ones are revealed and interpreted.