The purpose of this study is to examine the sociocultural meanings of flapper look in American society during the 1920s. Using the ProQuest database, I searched articles from The New York Times published between 1920 and 1929 for opinions and discussions on the flapper look. Keywords included “clothing,” “dress,” “fashion,” and “flapper,” and advertisements and articles on menswear, leisurewear, and bathing suits were excluded. In the resulting articles, I extracted the following sociocultural meanings: autonomy, activeness, practicality, attractiveness, and extravagance. Meanings were analyzed from the opinions and discussions focusing on skirt length, dresses that directly and indirectly exposed the body, heavy make-up, non-constricting underwear, the H-line dress, bobbed hair, hygiene, comfort, and consumption. In sum, the 1920s flapper look represented progressive characteristics such as autonomous and active womanhood and practicality, which matched the technological development of the time. However, the flapper look was commercialized and exploited to make women look attractive and extravagant. Even though American women had access to higher education, more economic power, and suffrage in the 1920s, they were limited in their ability to overcome social conventions and the power of consumerism. Understanding the double-sidedness of flapper look within the social context of the time would enhance the comprehension of the relationship between women’s lifestyles and changing fashion.