Critics find hipster style rife with irony, both intentional and unintentional, because it is an invented tradition, ungrounded in, and disconnected from, the hipsters’ true social status. Many of these critics see hipster beards as an example of this strained effort by young, educated urbanites to pretend not to be the superficial bourgeois consumers that they are. This chapter argues that, while hipster culture is certainly contradictory and problematic in many respects, the hipster beard, at least, is not simply an insincere ruse. The true irony of the hipster beard is that it is conventionally unconventional; that is, a performance of anti-fashion whose appeal to nature and autonomy is part and parcel of a time-honored and reliable cultural strategy in Western culture for defining an alternative, nonconforming masculinity.