: This study considers aesthetic characteristics by examining fashion style of fashion journalist Anna Wintour. Fashion journalists are specialists who work at fashion media. Especially, Anna Wintour is one of the most famous fashion journalist in the world and fashion icon, who has been editor-in chief of Vogue USA since 1988. For this study, Anna Witour's photograph was collected from 2010 to 2015 on web-sites. After collecting images, it analysed with 4criterions which were silhouette, color, fabric(pattern and texture) and hair style(and accessories) following advance researches analysis about fashion style. The conclusions of this study are as follows. First, symbolism revealed that could express her identity through utilizing steady items such as blond bob hair, Chanel bold sunglasses, short round neckless and Manolo Blahnik's low-heeled slingback nude sandals. Especially, she gave consistency to her fashion style with fixed hair style and accessories which are similar in shape. Second, femininity, that reveal as an internal characteristic such as sensitivity and as an external characteristic like fluidity. Anna Wintour expressed femininity with elegant curvy silhouette, various of color and flower pattern. Particularly, she emphasized nature women's body shape with princess silhouette, slim silhouette. Third, analysis result indicated characteristic of authority with oversize silhouette, wide lapel details and glamorous genuine fur items. Furthermore, some of her fur items looked overwhelming which dyed in artificial color or printed with leopard pattern. These powerful items contained immanent meanings that are power and position which could express a role as an editor-in chief of Vogue USA.