First Monday In May (2016)

We would be remiss if we didn’t include the 2016 documentary The First Monday In May, about the Costume Institute and Vogue’s work to organize the biggest night in fashion, celebrity, and art – The Met Gala. Likened to be the fashion industry’s Easter Sunday, The First Monday In May takes a look at the glossy, star-studded benefit as well as draws back the curtain to reveal the people that make it all happen. The documentary also takes a deeper look into whether fashion constitutes as Art, to which it swiftly responds in its opening scenes, through a montage of ornately designed garments that, of course, fashion is Art.

The Gospel According André (2018)

Exuberantly larger than life, André Leon Talley is a fashion exception for the way the 72-years old editor defied discrimination and elitism, rising to become the industry’s most recognised figure. Tom Ford remarks that Talley may be one of the last editors to have truly seen fashion in its heyday in the 70s. A revering figure, he recounts the illustrious career he has had at Vogue in this documentary.

Westwood: Punk, Icon, Activist (2018)

Fresh off the high of Cruella, Disney’s latest blockbuster to write the villain character a hero story, why not dive deep into the world of the punk predecessor herself? In the 70s, Westwood led masses to liberation in leather-clad looks and bold T-shirts – leaning into deconstruction as a tool of revolution. Her influence is almost ubiquitously felt in fashion, particularly in Cruella which sets Emma Stone’s character in the glam-punk world that Westwood helped pave. Learn about the icon’s journey to legacy in this documentary.

McQueen (2018)

Sad and celebratory and immensely moving, McQueen gives a personal look at the brilliant life and career of late British fashion designer Alexander McQueen, whose life was tragically cut short in 2010. This beautifully-produced film is a thorough, well-researched collection of exclusive interviews with his closest friends and family, recovered archives, behind-the-scenes runway shots, and magnificent visuals and music that paint a rags-to-riches story as bold and raw as McQueen’s own world of savage beauty.

Alexa Chung: Future of Fashion (2015)

Appealing to a new generation of content consumers, Alexa Chung’s YouTube docu-series Future of Fashion aims to “uncover the depth of the industry and the huge variety of roles that go towards sending clothes down the catwalk season after season.” Presented in digestible 10-15-minute video episodes, Future of Fashion explores everything from how to get a job at Vogue to blogging and building your own platform. Chung bolsters her investigation with access to the industry’s biggest names and a finger on the pulse of the biggest topics of the moment, whether that’s fashion sustainability and technology or trend forecasting.

Dior and I (2014)

Frédéric Tcheng’s Dior and I takes viewers inside the fantastical world of Christian Dior during the creation of Raf Simon’s first haute couture collection in 2012. From Simons’ first day at work to the official runway premiere, this eight-week-long journey traces moments of both great self-confidence and self-doubt with a sense of history and a feel for the relentless pace of work inside the atelier. In addition to Simons’ narrative, the film shines a light on the dedicated designers and seamstresses that bring to life the artistic director’s visions, panning through the elegant halls of the Maison to the big reveal at the show.

Iris (2014)

Legendary documentarist Albert Maysles paints a visually stunning character study of one of New York City’s biggest personalities — 97-year-old style icon Iris Apfel, whose oversized round black-rimmed glasses and eclectic sense of style has made her one of the industry’s most recognisable tastemakers. Inside her maximalist world, we witness the tact and dedication Apfel puts into finding her objects, as well as the sheer volume of clothing and jewellery that leans on the side of hoarding. More than a fashion documentary, Iris tells the story of a free spirit and her undying love for fashion, art, creativity and the people that surround her.

Diana Vreeland: The Eye has to Travel (2011)

In an era before world-famous fashion personalities and editors was Diana Vreeland — editor-in-chief of Vogue during the 1960s and one of the most colourful characters of the 20th century. Diana Vreeland: The Eye has to Travel gives a glimpse into Vreeland’s extraordinary life, rich with stories of extravagance and excess, transporting viewers to her upbringing in Paris during the Belle Epoque and New York City in the 1920s. The documentary highlights Vreeland’s many fashion achievements, such as discovering Twiggy and Lauren Bacall, advising Jackie Kennedy on style, and transforming the Met Gala into the blockbuster event it is today. But it is her large-than-life vision and cutting wit that takes front seat.

Bill Cunningham New York (2010)

The late Bill Cunningham was (and always will be) the ultimate chronicler of fashion on the streets. For several decades, Cunningham devotedly snapped photos of New York’s most interestingly dressed individuals — high society and normal folk alike — to document real fashion as it happened for his New York Times Style columns “On the Street” and “Evening Hours.” This affectionate documentary paints a touching, gently humorous portrait of Cunningham’s modest charm and work ethic while giving a rare glimpse into his private life and the people whom he closely worked with. “We all get dressed for Bill,” says Anna Wintour.

The September Issue (2009)

R.J. Cutler’s The September Issue follows American Vogue editor in chief Anna Wintour and her team of editors as they create the September issue for 2007, which, weighing nearly five pounds, was at the time the single largest issue of a magazine that had ever been published. This behind-the-scenes documentary studies the forces, passions and hard work behind the world’s biggest fashion magazine, giving a fly-on-the-wall portrait of its influential figures and their critical moments of harmony and disagreement.

Paris Is Burning (1991)

Before there was the 2019 Met Gala Camp: Notes on Fashion, RuPaul’s Drag Race, and Pose, there was the 1990 cult documentary Paris Is Burning. Shot over a period of seven years, director Jennie Livingston documents New York’s vibrant ballroom subculture during the mid-to-late 1980s, at a time of heightened ideals of wealth and glamour, when socially-shunned communities participated in dance/catwalk “balls” inspired by the world of fashion. Between vibrant scenes of vogueing and “throwing shade,” individual narratives of struggle, resistance and passion demonstrate the importance of challenging conventional standards of beauty and taste, as well as the role marginalised communities played in the history of fashion and art.