Required Viewing: Movies About Fashion

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To the delight of New Yorkers, Times readers, and street fashion fans alike, tomorrow brings the release of Bill Cunningham New York , a documentary about the bicycle-riding octogenarian whose photo collages have long been the best thing about the Styles section. Although he’s been on the scene for over four decades, Cunningham is a notorious loner, and this film — featuring interviews with everyone from Anna Wintour to Tom Wolfe — will be most fans’ first beyond-the-byline look at the photographer.

In celebration of Bill Cunningham New York, and because as far as we’re concerned, few things go together as well as film and fashion, we’ve compiled a list of fashion-themed movies you need to watch. From classic to campy, our picks are after the jump.

Blow-Up (1966)

Ever wonder why so many Italian movies of the late ’60s and early ’70s were so obsessed with the fashion industry and the models who populate it? It probably had something to do with Michelangelo Antonioni’s 1966 mod masterpiece, Blow-Up. The renowned filmmaker’s first English-language feature follows a hedonist British fashion photographer who takes a photo of something he shouldn’t have seen. Honestly, this may be the coolest film of all time.

The Devil Wears Prada (2006)

The film adaptation of Lauren Weisberger’s dishy novel about life as Anna Wintour’s assistant at Vogue may not be classic cinema, but it’s a whole lot of fun. While Anne Hathaway is good as idealistic, bookish, overworked Andy, it’s Meryl Streep as heavily Wintour-inspired ice-queen editrix Miranda Priestly who makes the movie a joy to watch.

The September Issue (2009)

Devil Wears Prada audiences curious about what makes the real Anna Wintour tick got a chance to see her up close and personal in this documentary, which follows the Vogue staff as they put together the year’s biggest and most important issue. Although all kinds of boldface fashion names (Karl Lagerfeld, Jean-Paul Gaultier, André Leon Talley, etc.) make appearances, it’s creative director Grace Coddington, whose romantic aesthetic often clashes with Wintour’s bottom-line sensibilities, who becomes the film’s true star.

Unzipped (1995)

A veritable Truth or Dare for the fashion world, Unzipped documents flamboyant designer (and, most recently, a judge and mentor on Bravo’s The Fashion Show) Isaac Mizrahi as he puts together in fall 1994 collection. From Mizrahi’s big personality to the supermodels who populate the film (Naomi! Cindy! Linda! Kate! Padma!) to the ’90s fashion nostalgia, this one is great late-night viewing. Unfortunately, Mizrahi wasn’t as big a fan of Unzipped as we are. The film was directed by his then-boyfriend, Douglas Keeve, and the couple eventually broke up because of it.

Valentino: The Last Emperor (2008)

Some of the films on this list could convince you that everyone in fashion is a hateful narcissist with a heart of polished stone. Valentino: The Last Emperor is the antidote to that. This documentary follows one of our greatest living fashion designers as he prepares for a 2007 show that was both a tribute to a career that spanned five decades and Valentino Garavani’s professional swan song. What makes it truly unique (and heartwarming) is its tender, nuanced depiction of the 50-year relationship between Valentino, the aesthete, and Giancarlo Giammetti, his practical-minded partner in business and live.

Coco Before Chanel (2009)

Coco Chanel is one fashion’s all-time most fascinating figures, so it makes sense that there have been tons of movies about her. Our pick is the recent French flick Coco Before Chanel. Audrey Tatou stars as the young Gabrielle Chanel, a lounge singer and seamstress who slept her way into high society before meeting the man — and finding the career — she loved.

Zoolander (2001)

Try as he might to cross over to more serious roles (hey, Greenberg), it’s looking more likely every year that Ben Stiller’s most memorable character will be Derek Zoolander — a vain, dumb, orange-tanned, and completely hilarious male model a decade or so past his prime who allows himself to be dragged into an international assassination plot. You’ve got to see this farce at least once. The David Bowie cameo alone is well worth your time.

Mahogony (1975)

Campy but fun: Diana Ross stars in this Motown-produced, Berry Gordy-directed film about a poor girl from Chicago who must choose between a glamorous life as a top designer in Rome and the love of her life. Hey, the music is good.

Prêt-à-Porter (1994)

Prêt-à-Porter has the dubious honor of being one of Robert Altman’s worst films. Then again, we’d rather watch Altman at his worst than most directors at their best. Comprised of several vignettes that take place around a single Paris fashion show, the dark comedy is at least worth watching for its ensemble cast: Marcello Mastroianni, Sophia Lauren, Lily Tomlin, Forest Whitaker, Lauren Bacall, Tracey Ullman, and Julia Roberts all make appearances in the film.

Vidal Sassoon: The Movie (2010)

Plenty of fashion designers have earned their own documentaries, so how about a hairdresser? No one deserves one more than Vidal Sassoon, the man whose geometric hairdos — remember Vogue‘s Coddington modeling the iconic five-pointed bob? — defined ’60s chic. And the film, as Stephen Holden wrote in the Times, “isn’t just the story of a brilliant fashion idea that swept the globe. It is a euphoric account of one man’s strenuous self-invention.” Add to that the movie’s boatload of period glamor and it’s a must-see.