Starting with the assumption that media, particularly magazines, serve as a ground that shape the ideological landscape for women representations, this paper explores feminine ideologies and representations of twelve (12) Cosmopolitan Philippines magazine covers from the year 2015. Underlying ideological structures were found not only in the linguistic but symbolic features of the text as well. Employing the methodologies of multimodal critical discourse analysis, the investigation revealed emerging patterns on how women are portrayed and represented in the magazine covers. The “fun and fearless” catchphrase that the magazine has shaped to define the modern Filipina (a) presents them as hyper sexualized and practicing adventurous sex, (b) positions them as followers of health and beauty regimens and a glamorous lifestyle that ultimately lead to the affirmation of the opposite sex, and (c) objectifies them through come-hither poses and scantily-clad bodies that emphasize the cleavage, toned abdomens, and legs. The paper likewise considers the possible implications brought about by the perpetuation of these ideological structures.