The trajectory of a creative career is rarely a linear ascent. More often, it is a series of experiments in self-presentation — many of which are now preserved in the permanent archive of the early internet. A new feature in i-D gathers designers, musicians, and cultural commentators to revisit the aesthetic missteps that defined their formative years. The participants, including actor Sebastian Croft, musician Goldie, and designer Joyce Bao, treat these phases not as embarrassments to be buried but as essential chapters in the development of a professional identity.
The premise is deceptively simple: look back at your worst style choices and explain what they meant. The answers, however, reveal something more substantive about how creative people are formed. From emo bowl cuts to ill-advised wardrobe overhauls, the "cursed" looks catalogued in the piece function less as punchlines and more as evidence of a process — the slow, often painful calibration of an outward self against an inner sensibility that has not yet found its language.
The productive discomfort of not fitting in
Fashion and music have long mythologized the figure of the outsider, but the specific mechanics of that outsider status receive less attention. What the i-D feature surfaces is the role of active discomfort — not mere nonconformity, but the genuine social friction of getting it wrong in public. Designer Oscar Ouyang frames this as a tactical advantage: the person who does not fit in is forced to keep iterating, while peers who settle into convention early may plateau. The "ugly duckling" is not simply waiting to become a swan; the duckling is doing more reps.
This idea has deep roots in creative disciplines. The concept of the "beginner's mind" in design thinking, the deliberately bad first drafts championed in writing pedagogy, the rough demos that precede polished albums — all share the assumption that quality emerges from a willingness to produce work that is, by any reasonable standard, not good yet. What distinguishes the fashion context is that the medium is the self. The bad outfit is not a discarded sketch in a notebook; it is worn in public, photographed, and increasingly, indexed forever.
Joyce Bao's description of her move from Michigan to Shanghai as a period of "self-invention" underscores this point. Geographic displacement compounded the identity crisis already inherent in early adulthood, forcing a more radical set of experiments than a stable environment might have demanded. The result was not a smooth transition but a series of provisional selves, each one closer to a voice that could eventually hold.
Cringe as archive in the age of digital permanence
The digital dimension adds a layer that previous generations of creatives did not face. Writer Ashley Ogawa Clarke's recollection of an American Apparel-inflected "Goldsmiths era" and Croft's memory of a haircut that made him resemble a "38-year-old dance instructor" are not just personal anecdotes — they exist, or could exist, as retrievable images. Kim Russell's observation that even one's most questionable looks might now live on Getty Images captures a real shift in the stakes of experimentation. The awkward phase used to be ephemeral. Now it is a matter of public record.
This permanence creates a paradox. On one hand, the knowledge that every misstep is archived could discourage risk-taking, pushing young creatives toward safer, more curated self-presentation from the start. On the other, the normalization of the "cursed" photo — the willingness of established figures to publicly claim their worst moments — may function as a counterweight, granting permission to be visibly unfinished.
The tension between these forces is worth watching. A culture that demands polished personal brands from increasingly young ages sits uneasily alongside an industry that still depends on the kind of rough, unselfconscious experimentation that produces original voices. Whether the next generation of designers and musicians will have the space to be genuinely awkward — rather than performing a curated version of awkwardness — remains an open question. The i-D feature, at minimum, makes the case that the friction was worth it for those who endured it.
With reporting from i-D.
Source · i-D
