While most research on beauty and inequality focuses on socioeconomic outcomes, this chapter foregrounds the relation between beauty (or attractiveness) on various aspects of life satisfaction. Researchers have consistently found that more attractive adults also tend to be more satisfied with their lives. How are these two phenomena actually related? Some scholars argue that “subjective” conditions matter more for happiness: how people perceive their own attractiveness or body image directly impacts how satisfied they are in their lives. Other scholars argue that “objective” conditions matter more for happiness: body-mass index, assessments of attractiveness by independent reviewers, and other indicators outside of the respondent’s subjective perspective matter more for happiness because such attractive people are able to land better jobs or attract partners, for instance. We review existing studies to provide an overview of the different strategies and approaches used to estimate perceived attractiveness or beauty, as well as different measures for well-being. Using a special sample of PIAAC data in the Czech Republic, this chapter directly analyzes the role of objective and subjective dimensions of beauty and how they are mediated by other factors known to impact life satisfaction. Our analysis lends support to the “objective” view: individuals assessed by others as attractive are significantly happier in their lives than those perceived as less attractive. We also show that the effect of attractiveness is stronger for men than for women. We also find that a part of this effect is indirectly due to the higher self-esteem and stronger mental stability of individuals viewed as attractive by others. These results point to important new directions for future research, such as the possibility of comparative studies to assess how the relationship between beauty and well-being might vary by national or cultural conditions.