Interaction between fashion and personality is analyzed. There is fashion orientation specific for every stage of personal development - adaptation, individualization and integration. The types of fashion standard imitation on adaptation stage are shown by the authors differentiating learning and conformity imitation. There is possible individual way in upbringing and education on individualization stage. The problems of referentiality and of play-back in forming of aesthetical views are discussed. All the notions are illustrated by school experience. There are recommendations for the usage of fashion mechanisms in upbringing of adolescents.