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Even though fashion strives to be innovative and original, there is only so much that a designer can do to make their work distinct or eye-catching, and chief among these techniques is the opportunity to play with a garment’s cut. For the past decade or so, proportions on the runway have become more and more exaggerated, and suddenly, wildly oversized clothes have gone from shabby to chic. Picture the celebrities of yesteryear in contrast to modern tastemakers and you’d be hard pressed not to notice the eschewal of tailoring and form-hugging fashion for baggy t-shirts, hoodies, and slouchy trousers. From the days of flappers in the 1920s, to the radical re-imagining of the body by Rei Kawakubo and it-girls like Phoebe Philo and Stella McCartney, the history of oversized fashion is riddled with complicated politics and may be the most poignant intersection of gender, class, race, and clothes that we have examined.

Historians tell us that oversized or baggy clothes first came into popularity in the 1920s (at least in Western fashion). Post-war attitudes had shifted as the first women in Canada and the United States earned the right to vote and went to work. Much like their social positions, women’s clothing became far more mobile, and Coco Chanel was at the forefront of the movement to rid fashion of the austere, corseted styles of the previous generations. Liberation manifested itself physically in the relaxed fit of garments and with it came a new set of ideals for women; rather than wanting to look demure and delicate, the shapeless figure of flapper dresses and Chanel’s famous two-piece sought to minimize signifiers of overt femininity by flattening the appearance of breasts and hips.

The success of the oversized cut in the 1920s – particularly with its implications for women’s freedom – was repeated several times throughout the 20th century. In the late 70s, Diane Keaton’s Annie Hall became the cinematic fashion icon that she is today for her wardrobe of button-ups, padded tweed-blazers, and loose denim. Arguably a precursor to the wide-fitting power suit of the 1980s, Annie Hall once again played upon the idea of pairing a more liberal female attitude with traditionally masculine, loose-fitting fashion. The magic of this continued trend is that it made fashion a site where women had more choice to express themselves outside of the confines of a very strict gender binary; dressing ‘like a boy’ was (and to a great degree, still is) seen as a rejection of feminine beauty standards and therefore something like a political declaration. Much like the moniker of the famous Japanese brand Comme des Garcons (“like the boys”), more women were accessing the opportunity to both dress like men and occupy the same spaces as them in the workforce and in popular culture.

The challenge here, however, is that oversized fashion was seen as a method of both taking back ownership of the female body while simultaneously obscuring it; the replacement of ‘feminine’ signifiers with male ones in order to command respect means acknowledging female-ness as inferior. This creates a paradox of empowerment wherein women must conceal their femininity in order to be on an equal footing with men. Instead of embodying gender equality, by making the wearer appear more skinny, long, and ‘masculine,’ does oversized fashion merely reproduce it?

The double-standard with which oversized fashion is so often (ignorantly) analyzed also plays upon classism. Writer Tom Wolfe coined the term “radical chic” when describing the bohemian, thrifty hippies of the 1970s, whose style arsenal borrowed from the poor to clothe the wealthy. The latter sought to represent a more down-to-earth outlook, but the tradition of the rich copying the poor soon came into popularity and turned the fashion system on its head altogether. This is why, again, the inherent “cool” of an enlarged Céline suit retailing for $4200 is a paradox; on a skinny, rich, probably white fashion influencer or celebrity, this look is lauded as edgy and “now,” but a two-sizes-too-large sweatshirt on someone living in poverty is read as ill-fitting and shabby. The radical ‘it’-factor that we assign to wearers of oversized fashion is mediated by lenses of class, much like how our understanding of the relationship between cut and gender expression still clings to the underlying belief that gender is binary (it isn’t).

Likewise, in recent years, oversized fashion has found its way onto the runway by means of streetwear, a trend borrowed from skateboarding and early hip-hop culture. Kangol, Champion, and Timberland were once brands made popular by rappers and hip-hop artists in the 80s and 90s that are now ubiquitous throughout the fashion landscape. Streetwear’s most iconic export may very well be the hoodie, a style that has become a staple in the American wardrobe, but is still read differently depending on the body of the wearer; after the police shooting of young Trayvon Martin in February 2012, Martin’s hoodie became a symbol of the stereotypes that are still held against black men in the United States. Former-FOX News host (and human garbage fire) Bill O’Reilly famously said that the hoodie “made him look a certain way […] and that way is how ‘gangstas’ look,” prompting protestors to host a “Million Hoodie March” in New York City in memory of the slain teenager. In other words, Vêtements can parade a couture hoodie down the runway at Paris Fashion Week and be considered ingenious, but a 17 year old black boy is profiled and shot for wearing one in Florida. Our understanding of the hoodie then has to change as we reflect on how the style can be interpreted as “athletic,” “edgy,” or “dangerous” depending on the wearer and the various stigmas that are unfairly attached to them.

But such is the power of oversized fashion. It is astonishing how simply changing or emphasizing the cut of a garment has the power to complicate what we know about a person’s style, background, and beliefs. The history of designers who have pulled on exaggerated fits for inspiration could fill a book, and there isn’t one of us reading this who hasn’t enjoyed the cosiness and mobility of a good oversized sweater or t-shirt dress. But there is a need to be critical of how institutions sell us this style and the kind of language or references that they draw on when they do so, considering how oversized clothing has been used to both defy and reinforce social conventions over time.

Main Image via Céline SS17/Imaxtree


"90 Years of Fashion" by Annalee Gold

Annie Hall’s Lessons in Self-Directed Style

Radical Chic: That Party at Lenny’s

The Uncomfortable History of Hoodies

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