9 Must-See Fashion Films to Watch Before The First Monday in May

Earlier this month, The First Monday in May debuted at the Tribeca Film Festival. Created in partnership with Vogue and the Metropolitan Museum of Art, the movie takes a closer, behind-the-scenes look at the annual Met Gala and the 2015 show, China: Through the Looking Glass. It takes viewers on a ride, highlighting all of the planning that goes into the event, from meticulous details like napkin design, to make or break moments like Rihanna’s performance budget. But this isn’t the only film that gives you a realistic look at the fashion industry, there are a number of equally amazing documentaries that offer rare glimpses into the world of glamour, beauty and style.

The September Issue

If you liked the Devil Wear Prada, think of The September Issue as a more accurate and realistic look at the world of fashion publications. Revolving around Anna Wintour and her work at Vogue, the film gives the audience an inside look at not only the real Wintour, but the creativity, planning and power dynamic that goes into being one of the most influential women in the industry. From consulting designers prior to Fashion Week to creating an eye-catching cover, she creates the September issue, one of the biggest books of the year, from the ground up.

Bill Cunningham New York

If you love street style, then Bill Cunningham New York is a must-see. Regarded as the original street-style photographer, Cunningham was snapping photos of sharply dresses fashionistas for years before style blogs became a thing. The film focuses on his work and eye for creativity and fashion, but it also touches on the personal life and passion of this New York Times photographer. Winner of several awards including Best Storytelling for Documentaries at the Nantucket Film Festival and Best First Documentary at the Abu Dhabi Film Festival, it offers a private, rarely-seen look at the father of street style photography.

Dior and I

When Raf Simons was hired on as creative director at Dior, he was given a time frame of eight weeks to finish the house’s haute couture collection, something that most designers complete in a generous six month span. This documentary follows Simons during those first few months when he was trying to prove himself, find a balance between his and Dior’s designs, and create a collection in mere weeks. It offers a behind-the-scenes look at the famed French house that is rarely viewed by those outside the industry. Directed by Frédéric Tcheng, the film has won several major awards including the Official Selection at the Sydney International Film Festival, the Special Jury Award at the Seattle International Film Festival and a Special Recognition nomination at the Tribeca Film Festival.


There’s no one quite like quite like Iris Apfel. At 94 years old, the businesswoman, interior designer and style icon is one of the most notable women in fashion, well known for her eccentric dress and bug-eyed glasses. This documentary follows her fascinating journey over the decades from her position as interior decorator at The White House to jet-setting style muse. She talks about her extensive jewelry collection, her viewpoints on fashion and attitude toward personal style. “I can’t judge,” she tells the camera when asked why she never seems to dislike anyone’s outfit. “It’s better to be happy than well dressed.”

Mademoiselle C

After years as a model, writer and editor-in-chief of Vogue Paris, Carine Roitfeld decided to start her own magazine: CR Fashion Book. This documentary follows her process in creating her first issue, and taking steps out on her own after leaving the helm of Vogue. Viewers get a taste of what it’s like to be one of the most influential women in fashion, as the camera follows her from the front row of runway shows to celebrating the birth of her first grandchild. Fashion die-hards will want to pay close attention to this one—major names like Karl Lagerfeld, Bruce Webber and Linda Evangelista make cameos in this 93-minute who’s who of the industry.

Diana Vreeland: The Eye Has To Travel

As the first celebrity editor, Diana Vreeland was considered one most of the most influential women in fashion from the ‘40s to the ‘80s, pushing the boundaries for what was acceptable and en vogue at the time. She was credited with discovering actress Lauren Bacall and advising First Lady Jacqueline Kennedy in matters of style. After 25 years at Harper’s Bazaar and another eight at Vogue, she became consultant to the Costume Institute of the Metropolitan Museum of Art, and even after her death in 1989, maintains her position as one of the most beloved and influential editors in fashion. The film, which was made by the wife of one of Vreeland’s grandsons, offers an unflinching view at this power woman and a rich portrait of the history of fashion.

Valentino: The Last Emperor

Take a closer look at the life and times of designer Valentino Garavani and his longtime love and business partner, Giancarlo Giammetti. Showing glimpses of his private life—where he and Giammetti met, their homes and pets—it gives a rare peek into the lavish world that Valentino built for himself over the years. The film is set during Valentino’s final Haute Couture show, his last show before retirement, and highlights how the beauty and glamour of his heyday is now fading in the world of fashion. Directed by Frédéric Tcheng, the man behind Dior and I and Diana Vreeland: The Eye Has to Travel, the documentary was given numerous awards at the Venice, Chicago and Toronto International Film Festival.

Scatter My Ashes at Bergdorfs

Despite the somewhat morose title, Scatter My Ashes at Bergdorfs is actually a beautifully done piece on the wide-reaching influence and impact of the popular department store. From discussions of the annual Christmas window display to the services offered to their most notable customers, the film covers all of the eccentricities that make Bergdorfs a must-shop. It also offers a closer look at personal shopper Betty Halbreich, who has dressed celebrities, socialites and even assisted with choosing the clothes for Sex and the City. If you’re a fan of the fashion scene then keep your eyes out, celebrities, designers, models, stylists and influencers all make appearances in this film to declare their love for Bergdorfs.

L’amour Fou

Of all the fashion films on our list, L’amour Fou is decidedly one of the most heart wrenching. This documentary channels the life and times of Yves Saint Laurent by going into depth about his relationship with longtime lover and business partner Pierre Bergé. Rather than focusing too much on YSL’s designs (which most fashionistas are already familiar with) or on his gossip-worthy party life (he struggled with depression, drugs and alcohol), it finds a healthy medium through Bergé’s memories of their life together. It offers views a deeply personal and at times heartbreaking story that is told as Bergé auctions off their belongings after Saint Laurent’s death. This moving piece won the Fipresci International Critics prize at the Toronto International Film Festival and was an official selection at both Tribeca and the San Francisco International Film Festival.

Marissa Stempien

Marissa Stempien is a freelance writer and editor with a focus on travel, fashion, lifestyle, and culture. Her work has been featured in a number of print and online publications including ABC News, Popsugar, Huffington Post, JustLuxe, Luxury Living and CityGirlGoneMom. Marissa is an avid traveler and is always looking to visit somewhere new or unexplored. Her unique lifestyle has given way to her...(Read More)

Around the web