Although the structure of formal education may not be desirable – or available – to everyone, there’s something so satisfying about constantly finding new things to learn about. The best thing about life is how much it teaches you — and it’s even better when that learning barely costs you a dime. While many of us don’t have the time to cozy down with a new book each week, we very often do have enough time to Netflix and chill. And with a plethora of documentaries on streaming services like Hulu and Amazon, we really have no excuse not to watch. Thankfully, the internet (and the documentary world) are especially kind to fashion lovers, with a wide-range of docs to watch on everything from the beginning of voguing, to street style, to the life and times of some of the most iconic fashion designers out there.
If you’ve ever wanted to dive in headfirst to the world of fashion, but don’t know where to start, check out these nine documentaries to kickstart your journey.
1The September Issue
If you don’t know where to start, start here. Iconic in its own right, Vogue is the leader of everything fashion. Even with the rise of alternative, independent fashion magazines, Vogue continues to pave the way for fashion publications. The September Issue chronicles the making of the September 2007 issue, which was the largest single issue of a magazine ever published at a whopping five pounds. The documentary follows legendary editor-in-chief Anna Wintour and then creative director Grace Coddington as they navigate the making of the issue. Notable appearances include André Leon Talley, Oscar de le Renta, and Jean-Paul Gaultier.
Watch if: You want to work in the magazine industry or if you want to see what the real Anna Wintour is actually like (she’s not as intimidating as you think!)
2Diana Vreeland: The Eye Has to Travel
One of the most iconic fashion editors of all time, Diana Vreeland was known for her unapologetic and opulent opinion — and, of course, her style. Diana’s whole shtick was to take what makes you different and run with it. Diana Vreeland: The Eye Has to Travel does an excellent job of covering the editor’s early life, from her start as a fashion editor at Harper’s Bazaar to her eventual role as editor-in-chief of Vogue. Diana was the first true fashion editor, changing the way we interact with the industry. This documentary weaves together footage of the real Diana to create a telling story of how she became so influential.
Watch if: You need a new style icon to love, or if you just want to know about the fashion industry at the beginning of the 20th century.
3Dior and I
Although he may not be at the helm of the brand anymore, Dior and I follows Raf Simons as he makes his couture debut at the house of Dior. The documentary takes a real look into the world of couture, and what it means for a new designer to find his footing in one of the most established fashion houses in the industry. Although Simons is a part of the doc, it really follows the team in the atelier who create the pieces. Dior and I takes a personal approach to the long and grueling process of putting a couture collection together, giving us an intimate peek into the industry that we very seldom see. Highlights include footage of Simons before his first model is sent down the runway; raw, real, scared. More than anything, the film shows that it takes teamwork to turn the dream into a reality.
Watch if: You want the inside scoop of what it’s like in one of the most established couture houses in the world.
4Bill Cunningham New York
Where would all the street style stars be without Bill Cunningham? The legendary fashion photographer, famous for capturing the streets of New York, was as known for his eye as he was for his blue jacket and bike. Although Cunningham passed away last year, his legacy lives on thanks to this documentary. Bill Cunningham New York chronicles Bill as he takes photos for his columns in the New York Times Style section, “On the Street” and “Evening Hours.” With testimonies from New York favorites like Anna Wintour and David Rockefeller, the film chronicles Bill’s work as NYC’s greatest social anthropologist.
Watch if: You’re secretly a street style star.
“More is more and less is a bore,” says the iconic and flamboyant Iris Apfel. In her documentary, aptly titled Iris, we get a sneak peek into the wonderfully curated world of New York’s beloved fashion icon. Iris got her start as an interior designer, but was noticed for her eccentric style and unapologetic attitude. The documentary recounts Iris’s rise to fashion fame, giving viewers an inside look into her extravagant and dreamy life.
Watch if: You need a reminder that fashion is supposed to be empowering, personal, and FUN.
6This is My Dream
Fashion designer Yohji Yamamoto is known for being fiercely private, which is why This is My Dream is a must see. Yohji let his guard down for this, allowing a glimpse into a life that we can only imagine, from Tokyo to New York. The documentary chronicles the creation of a season of his Y-3 collection, which is in collaboration with Adidas. The line is hailed as “the future of sportswear,” and is ushering in a new era of fashion, tech, and activewear with style. The legendary designer is known for his compelling, sculptural work that feels more like art than fashion. This film is a peek inside his creative process.
Watch if: You want to feel like a fashion insider, and get an inside look into one of the most mysterious fashion houses out there.
If you know anything about fashion, you’ve probably heard the name Yves Saint Laurent — or at least seen his famous initials, YSL. L’Amour Fou recounts memories of the famous couturier who died in 2008. Although his fashion house is one of the most successful of all time, Yves dealt with depression for much of his life. Pierre Bergé, his business and life partner for half a decade, is the one who chronicles his life in this documentary. This film revolves around the 2009 auction that happened after the designer’s passing, when Bergé and his treasures were sold. The film is less of a retrospective and more of Pierre telling personal memories of his time with Yves, so make sure you have some tissues ready.
Watch if: You want a personal glimpse into the life of Yves Saint Laurent.
8Paris is Burning
One of the most seminal documentaries of all time, Paris is Burning chronicles the voguing and drag scene of New York in the 1980s. The film feels personal and inviting, exploring drag culture and the drag balls that allowed many to find acceptance when they often didn’t find it anywhere else. The film focuses on the LGBTQ+ subculture during the latter half of the decade, examining the opulence, glamour, and personal stories of many drag queens and voguing superstars who were staples in the circuit. Although it’s not necessarily a “fashion documentary,” Paris is Burning is a must see for every fashion loving person. Not only because the costumes and looks in it are inspiring, but because these are the men and women that have paved the way for what fashion looks like today.
Watch if: …Well, this is pretty much required viewing for anyone even remotely interested in fashion or drag culture. It’s iconic and deserves to be appreciated!