When we think of Tolstoy we picture a man who looks as far from a typical Russian nobleman as possible: bearded and wearing peasant-style clothes. This chapter examines the clothing choices Tolstoy made throughout his life and sets them in the contexts of imperial dress codes and his own thinking about Christianity and his place in the world. After Peter the Great introduced European dress for the nobility in the early eighteenth century, a large cultural divide developed between peasants and nobles. Tolstoy grew up wearing the clothing of the European elite while the peasants on his family estate wore more traditional Russian dress. However, in the 1860s Tolstoy began to wear a peasant-style beard and long, loose shirts, albeit made from more luxurious materials than were worn by the peasants themselves. Then, in the 1880s he began to make his own leather boots. This was all part of his broader philosophical project and attempt to lead a simpler, more Christian life. Though Tolstoy’s lifestyle choices often made things more difficult for his family, he nonetheless inspired many followers who imitated his dress style.