Fashion & Beauty

Films in Fashion

By Janet Kelly

IF YOU’RE impatiently waiting for who’s going to win best actor and what movie will get the nod for 2022’s top picture at the Oscars on March 12, here’s a thought: Curl up this last week of February/first week of March with one or three of these stellar documentaries and films about the fashion world.


2023’s Metropolitan Museum of Art’s first Monday in May event, otherwise known as the Met Gala, which benefits the museum’s Costume Institute, will take place May 1, a mere two months from now. The theme will be “Karl Lagerfeld: A Line of Beauty.” Suggested dress is anything Karl.

No invitation? You can still get a peek into the fashion world’s equivalent of the Super Bowl with the 2016 documentary The First Monday in May. The film follows the behind-the-scenes creation of the museum’s most attended fashion exhibition in its history: In 2015, “China Through the Looking Glass” showed how Western designers, such as John Galliano (whom curator Andrew Bolton interviews), Yves Saint Laurent and Jean Paul Gaultier, were inspired by Chinese art, film and culture. Every detail from the exhibition’s design to the must-see Red Carpet (what celebs wear what high-fashion gowns) to the floral arrangements and table settings is meticulously planned and executed by Vogue’s Anna Wintour and her team. It’s a treat for fashion lovers, maybe too inside baseball for others. Nevertheless, the breathtaking beauty of the clothing is what makes the film worth the watch.

First Monday in May is available to rent on Amazon Prime for $3.99. 


Halston, the documentary, tells the story of the rise and fall of the designer’s (born Roy Halston Frowick) fashion empire. To his detriment, Halston was way ahead of his time with ideas about clothing and business. He had an amazing eye, sense of proportion and ability to cut fabric without zippers or buttons. As his close friend Liza Minnelli, said, “His clothes danced with you.”

Despite his reputation as a heavy drug user, it wasn’t until he was middle-aged in the late ’70s and ’80s, when the business pressures were extremely stressful. He was rather a workaholic throughout his career.

Having started out as a milliner (famous for designing the pink pillbox Jacqueline Kennedy wore to her husband’s 1961 inauguration), he made a gigantic leap into unstructured, fluid clothing. He made a lot of money and then lost it all when he gave away the store and his name (without understanding the consequences) to investors. He died of AIDS far away from New York and the fashion industry —a rags-to-riches tale and then back again.

Watch the trailer here. The documentary is available on Apple TV for $9.99.


A 2009 American documentary film directed by R.J. Cutler, The September Issue is about the behind-the-scenes drama following editor-in-chief Anna Wintour and her staff during the production of the September 2007 edition of American Vogue.

Known for its number of ads; the 2007 edition weighed in with 840. Needless to say, it’s the biggest money maker of the year. With the stakes high, there’s even more tension than usual to make it fabulous.

And it’s complicated—deciding on the stories, choosing the clothes and models to wear them, picking the photographers, arranging the photo shoots in locations all over the world and then there’s the all-important cover.

Anna and Grace Coddington, Vogue’s longtime creative director both started working for Vogue the same day in 1988. They’re the main protagonists in the film, frequently butting heads on the issue’s contents.

Speaking directly to the camera, the two reveal some personal stories. Grace felt she had to escape her small town in Wales; she became a model and then when a bad accident left her scarred worked her way up the ladder at British Vogue before arriving at American Vogue. On a train heading to a shoot, Grace calms herself by looking out the window: “A photographer taught me to keep my eyes open at all times, that whatever you see can inspire you.” Anna talks about asking her father to help her decide on a career path. The British newspaper editor told her she was going to be the editor of Vogue. She also speaks about her three siblings and their impressive jobs and sheepishly says she thinks they’re amused by what she does.

You can watch The September Issue on YouTube.


Richard Press’s 2010 documentary, Bill Cunningham New York, profiles the quintessential chronicler of street style in New York City. Like Halston, he began his fashion career making hats. After his U.S. army service in Korea, he returned to write fashion for the Chicago Tribune and then Women’s Wear Daily in New York, where he quit when an editor completely changed the story Bill had written, making fun of his subjects’ clothes and appalling the good-natured Cunningham.

Gifted an Olympus camera by a London photographer, Cunningham found his niche. He realized that “the street was the missing ingredient” to see how people interpreted the clothing they wore. Plucked by the New York Times in the early ‘70s, he spent decades working on his columns “On the Street” and “Evening Hours.” He photographed uptowners (Anna Wintour, Tom Wolfe, Brooke Astor), downtown eccentrics (Annie Flanders of Details and founding editor Kim Hastreiter of Paper magazine)—who all show up in the film—and everyone in between. One humorous and touching moment is a scene at a surprise 80th birthday party for Cunningham,  where the Times staff wonders why Bill’s the only one who always gets his way.

A short question and answer with Cunningham, filmed in his Carnegie Hall studio/apartment (with no kitchen and no private bath) and only work-filled filing cabinets as furniture, reveals a sensitive, humane man completely dedicated to his art.

Bill Cunningham New York can be streamed on HBO Max.


Jeremy Piven as Harry Selfridge in front of his eponymous Oxford Street store. 

The television series, Mr. Selfridge, recounts the real-life story of the visionary  Harry Gordon Selfridge, who, after a successful retail career in Chicago, arrives with his family in 1909 London on a mission to transform the shopping experience on Oxford Street. And that he did: He rearranged the store’s layout to match what women wanted, moving makeup and perfume counters to front and center. He believed items should be accessible and be touched by customers. He wanted everyone to come to his store, regardless of class and was the first businessman to offer bi-annual sales and create a bargain basement. Decades ahead of his time (think Marvin Traub of Bloomingdale’s), Harry turned Selfridge’s into a destination where people could stay all day going to restaurants, hairdressers, galleries and more. He spent a cool $2 million on advertising for the store’s opening.

Though a brilliant salesman and born risk taker, after his wife dies, he eventually gambles too much, leading to his self-destruction and firing from the place he founded.

Watch Mr. Selfridge on Apple TV for $19.99 a season.


Reynolds Woodcock  fits Alma for a dress in Phantom Thread

Director Paul Thomas Anderson’s eighth feature is a film that spins an eerie web of a story, depicting a cat-and-mouse battle between fictional 1950s London dressmaker, the imperious Reynolds Woodcock (Daniel Day-Lewis) and an awkward waitress-turned-lover-and-muse, Alma Elson (Vicky Krieps). The third character in the triangle is Woodcock’s sister Cyril (Lesley Manville), who runs his business and social life, quickly dispatching the short-lived love interests of her brother.

When Alma’s spell wears off—Woodcock tires of her asserting herself and she’s on the brink of being forced out—she insists on staying as a member of the household. With the help of a mushroom omelet, the unexpectedly cunning Alma succeeds in turning the tables and subduing Woodcock to her will.

You can rent Phantom Thread on Amazon Prime for $3.99.



MyLittleBird often includes links to products we write about. Our editorial choices are made independently; nonetheless, a purchase made through such a link can sometimes result in MyLittleBird receiving a commission on the sale, whether through a retailer, an online store or

2 thoughts on “Films in Fashion

  1. Nancy G says:

    The closest I’ve come to watching a fashion movie is probably “The Devil Wears Prada,” although we did watch the Selfridge series. Anna Wintour has always fascinated me though, for some reason. Think I’ll pull up some of the ones featuring her. Thanks for the reviews and ideas.

    1. Janet Kelly says:

      I think The September Issue gives more insight into Wintour.

Leave a Reply

Your email address will not be published. Required fields are marked *