This study examines print advertising from Cookie, an up-scale American parenting magazine for affluent mothers. The ads include seven designer clothing brands: Rocawear, Baby Phat, Ralph Lauren, Diesel, Kenneth Cole, Sean John, and DKNY. When considered within the context of their adult equivalents, the ads for the children’s lines often created a prolepsis—or flash-forward—by depicting the child model as a nascent adult. This was accomplished in three ways. First, the children’s ads typically contained structural continuities such as logo, set design, and color scheme that helped reinforce their relationship with the adult brand. Second, most of the ads place the camera at eye-level—a framing that allows the child models to address their adult viewers as equals. Finally, almost half of the ads feature at least one child looking directly at the camera with a serious expression. This is significant because, in Western culture, the withholding of a smile is a sign of dominance typically reserved for adult males. When children mimic this familiar and powerful “look,” they convey a sense of adult-like confidence and self-awareness often associated with precocious sexuality.