This research paper investigates Gibran Khalil’s simplicity in The Wanderer as a stylistic feature which represents artistic values intended by the original author compared to the high formal style of the translator in the TT according to Newmark's communicative theory. The ambiguity of meaning and the misunderstanding that came out from using highly formal choices in the translation instead of simple language; the intended function by the original author; are the core of this study. The study includes content analysis of ten random selected examples from the parables and was based on Bell (1991: 186); Tytlor (1907 and 2007); Alosh (2005:1-17); Libo Huang (2015); Landers (2001: 7); Newmark (1981&1995); Baker (2000); Abdullah Shunnaq (1994) and Bastin (1998:7). The Study concludes that the translator uses highly formal equivalents which change the style of the origin. This way of style shifting leads to a loss of the artistic value of the simplicity of Gibran. Simplicity as a stylistic feature of the ST leads the reader of the TT to a misunderstanding and ambiguity.