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The 5 Best and Most Timeless Fashion Documentaries to Watch
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The 5 Best and Most Timeless Fashion Documentaries to Watch

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Fashion may come and go but fashion documentaries remain eternal.

Put on your fanciest sweatpants, pop some champagne and popcorn and settle in for the 5 best and most timeless fashion documentaries to watch.

The links have been updated since the Blog's original posting. Some movies can be streamed while others you might have to buy the old fashioned way on Amazon or access your local library to rent. 



Go big or go home. Iris Apel is the fashion, interior design and style icon known for her big round black eye glasses and larger than life costume couture jewelry. This documentary peeks into her life, how she adds to her eclectic selection of clothing, jewelry, accessories, and home design, and her theory on the truth and poetry of style. Iris remains a fashion icon at 98 years young today. Iris was released in 2015 but remains in style. 

Watch Iris on Amazon Prime here

Watch the trailer here

Pro tip: If you are someone that loves accessories, you will love this documentary. And if you are someone who has a lot of accessories that you pair with outfits, you will love The Hanger Valet to keep you organized on the daily or when traveling.   

Scatter My Ashes at Bergdorf’s  

As the rise of online and boutique retailers fuel the fashion world of today, it is important to pay respect to the department stores that were the pioneers of the retail world. Bergdorf Goodman is arguably the epitome of New York City. To designers, if your clothing is not carried at Bergdorf’s, then “you have no future” Isaac Mizrahi. Go behind the windows and into the heart of what makes the store tick in this oldie (2013) but goodie documentary.

Watch Scatter My Ashes at Bergdorf here

Watch the trailer here


Bill Cunningham New York  

Which came first: street style or Bill Cunningham and his camera? Even Anna Wintour was eager to be captured by the click of Bill’s camera. This street style fashion documentary tells the tale of how an unassuming man rolling around NYC on a bike and in his now famous blue raincoat drove the street style fashion world with his eye for style. Bill passed away in 2016 but his memory lives eternal with this film.


Watch Bill Cunningham New York on Amazon Prime here

Watch the trailer here


The September Issue  

Anna Wintour is the boss of fashion, obviously. Go inside the world and behind the cover of Vogue and what it takes to put out the biggest fashion issue of the year. This 2009 documentary never goes out of style because as Anna says “Fashion is not about looking backward; it’s about looking forward.”

Watch The September Issue on Amazon Prime here

Watch the trailer here


First Monday in May  

If you missed seeing the fashions at The Met Gala this year due to Covid, then sink in for this documentary from 2015 which follows the planning and execution of the show China: Through the Looking Glass. Can fashion be art? The First Monday in May makes the case that it can and does. Go behind the scenes to see what goes into planning and executing what André calls the Super Bowl of social fashion events.

Watch The First Monday in May on Amazon Prime here

Watch the trailer here


There are a handful of documentaries I love that I can't easily produce streaming links for. But if you are up for the challenge, you might love these as well: 

House of Z: The Zac Posen Documentary 

Diana Vreeland: The Eye Has to Travel 

Dior & I