When you need to feel fabulous for a few hours, there’s nothing quite like throwing on a fashion documentary. Something magical happens when you mix oodles of eye candy with the wonder of creative expression and a sprinkle of drama. The most memorable fashion documentaries master visual storytelling that is deeply invested in the subject while showcasing the bigger role fashion plays in how we view ourselves and the world around us. The 10 films in this list radiate the power of creativity and authenticity, whether exploring the lives of designers and fashionistas or taking a behind-the-scenes look at the industry’s cultural pillars.
While not all fashion stories have a happy ending, these 10 uplifting fashion documentaries are ready elevate your mood and your personal style.
1. Iris (2014)
It’s impossible not to smile while watching Iris Apfel just be herself. She exudes a smart, unpretentious charm that is simply irresistable. While so much of fashion feels like unobtainable perfection that requires substantial wealth, Iris’ perspective on personal style is a breath of fresh air – especially for maximalists. There are never too many bracelets, necklaces, patterns, colors. For Iris, real style is all about finding your own voice and leaning into the joy of creating a look you love. It’s mixing a vintage Yves Saint Laurent coat with thrift store dress and stack of rhinestone bracelets from Claire’s. Artfully directed by Albert Maysles (Gimme Shelter and Grey Gardens), watching Iris’s journey from interior design legend to fashion maven to international icon is both endearing and massively entertaining. Whenever I’m in a bad mindset or feeling too self-critical, this movie is my go-to mood booster.
2. First Monday in May (2016)
The Met Gala may have started as an annual fundraiser for the Costume Institute at the Metropolitan Museum of Art, but has since become a yearly cultural touchstone, complete with red carpet coverage that mirrors the Oscars. First Monday in May captures the ups and downs between The Met, Anna Wintour, curators, and Vogue staff as they plan, fight, freak out and ultimately pull off The Met Gala’s wildly successful 2015 exhibition ‘China: Through the Looking Glass’. Along with an inside view into crafting both the exhibit and the infamous party, the doc is chock full of gorgeous gowns, famous designers (Michael Kors, Jean Paul Gaultier and Karl Lagerfeld), and A-listers dripping in drool-worthy looks from Kate Hudson to Rhianna.
3. Advanced Style (2014)
Style doesn’t have an age limit, and Advanced Style reaffirms the joy of getting all dressed up just because you feel like it. Based on the popular blog of the same name by director Ari Seth Cohen, the film follows seven eclectic New York City women (ages 62 – 95), as they share their personal stories, incredible outfits, and style philosophies. While the fashion industry typically ignores women who have matured out of their ingenue years, Advanced Style celebrates the glamour and confidence that comes with experience. The film is also an important reminder that women are fabulous at every age and that the best part of being a grown up is dressing exactly how you want.
4. Bill Cunningham New York (2010)
If you need wholesome content, look no further. Everyone loves Bill Cunningham, the famously humble (and equally iconic) photographer for The New York Times‘s Style section. He spent decades capturing street trends from everyday New Yorkers then biking his way to Manhattan’s most exclusive society galas. In every shot and interview, there’s an infectious joy so inherent to Bill’s character that it rubs off on everyone around him. He loves taking pictures of stylish women, and that passion has resulted in decades of joyfully captured images that chronicle the evolution of American fashion. Anna Wintour even appears for an interview and actually smiles. If Anna’s having a good time, we all are.
5. Westwood: Punk, Icon, Activist (2018)
Vivienne Westwood’s influence is too big for a single film, but this intrepid doc does a great job of introducing audiences into the many lives of a brilliant designer. Westwood was a singular visionary whose influence shaped British culture far beyond her punk roots. The film follows her working-class upbringing and decades-long career from designing for the Sex Pistols to running a global fashion empire and her passion for political and environmental activism. While Westwood’s story is one of numerous successes and failures, the documentary focuses on the woman behind the clothes, and she’s a wonder to behold.
6. Dior & I (2014)
The emotionally riveting Dior & I follows the creation of Raf Simons’ first Haute Couture collection for the legendary house of Dior as Artistic Director. The beautifully shot film explores the designer’s full creative journey, from his first meeting with the atelier team in Paris to the highly anticipated runway show. The narrative is instantly compelling. Even audiences outside the fashion world are given enough background to appreciate the inherent pressure of a relatively unknown designer creating his first collection for such an iconic, international fashion house. The true joy of the film however, is that it spends just as much time showcasing and celebrating the talented team of craftspeople at Dior who construct and tailor every garment to perfection.
7. The September Issue (2009)
AKA, the movie that let the non-fashion world fall in love with Grace Coddington, the film follows Anna Wintour and Vogue’s harangued staff as they put together 2007’s September issue, the largest (and therefore most important) Vogue issue of the year. There are racks and racks of gorgeous clothing, glamorous photoshoots from NYC to Rome, and plenty of behind-the-scenes drama. The film also features an array of famous faces like Oscar de la Renta, Karl Lagerfeld, Sienna Miller, and Vera Wang.
8. Diana Vreeland: The Eye Has to Travel (2011)
There are women who create the life they want, there are women are women who craft their own mythology – and then there’s Diana Vreeland. This bombastic documentary follows the fascinating life, truths and untruths of the most influential fashion voice of the 20th century. Every inch of this documentary is filled with celebrity interviews and over-the-top stories, while simultaneously cataloging the progression of American fashion. From her trailblazing editorial roles at both Harper’s Bazaar and Vogue to revolutionizing the Costume Institute at the Metropolitan Museum of Art, Diana Vreeland is one of the most captivating subjects a film could ask for, and this film delivers on every level.
9. Scatter My Ashes at Bergdorf’s (2013)
Some documentaries offer an honest, unflinching look at their subject matter and some documentaries are more interested in selling a legacy. Enter the latter. Scatter My Ashes at Bergdorf’s may not provide a serious historical record of New York City’s most iconic luxury department store, but delivers a fun and uplifting watch nonetheless. The film equivalent of a coffee table book, the documentary features delightful anecdotes and insights from celebrities, Bergdorf employees, and fashion historians that celebrate impact of this one-of-a-kind institution.
10. Diane von Furstenberg: Woman in Charge (2024)
Diane von Furstenberg is one of the most famous names in fashion, and this documentary celebrates her fierce desire to live an authentic creative life. The film goes all in on the invention of the wrap dress and sensational rise of DVF as a revolutionary American brand along with Diane’s headline-grabbing personal life, from marrying an actual prince to partying at Studio 54. There’s tons of celebrity-fueled stories, gorgeous archival footage, and first-person interviews that allow Diana to share her story in her own words. While more reverential than introspective, the film shines a much-deserved spotlight on one of the most dynamic designers in American history.
Allison Goldstein 