Celebrities play an important role in setting the fashion agenda. Albeit often with some delay or in a watered-down form, celebrity trends are often embraced by either high street stores or more specialist fashion retailers. Designers often seek to push the boundaries of what is deemed possible in women's wear. Celebrity appearances, in particular at red carpet events, have in recent years featured increasingly daring ways of attracting attention to both the wearer's body and the designer's outfit idea. Nipple flashing has been usurped as the limit of daringness by an increasing focus on below the waist. Buttocks and the groin have become important areas for designers to flirt with, and in some cases reveal candidly. Meanwhile, designers offer increasingly extreme versions of that women's staple fashion item, the high-heeled shoe. This article presents an overview of some of the most daring celebrity fashion trends of recent years, provides cultural and aesthetic analysis on these trends, and comments on how these trends either currently do or in future may transfer to a broader clientele.