The 6 Most Fashionable Films From the 'Once Upon a Time in Hollywood' Era

6:15 AM 7/27/2019

by Vincent Boucher

The year 1969 was a watershed moment for movie style, from 'Easy Rider' to ''Sweet Charity' to 'Midnight Cowboy.'

From left: 'Easy Rider,' 'Sweet Charity,' 'Midnight Cowboy'
From left: 'Easy Rider,' 'Sweet Charity,' 'Midnight Cowboy'
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In Once Upon a Time in Hollywood, costume designer Arianne Phillips has pulled off a fond recreation of Tinseltown fashion in 1969. But when Angelenos were going to the movies themselves that year, what kind of styles were they seeing up on the big screen? Much like Quentin Tarantino’s film today, those movies were in their own way beginning to illustrate the chasm between Old Hollywood, the “dirty hippies” — as Leonardo DiCaprio's character calls them in the pic — and other burgeoning counterculture movements of the '60s. 

Of course, old traditions die hard, and the 1970 Oscar for best costume design for the films of the previous year went to the epic Anne of the Thousand Days and its little-known British costume designer Margaret Furseupholding the still-frequent Academy habit of rewarding historical warhorses over films that feature contemporary clothes. (Presumably Anne beat out the other lavishly appointed retro nominee of the year, Hello Dolly and its famed designer Irene Sharaff.) The competing nominees were veteran Edith Head for Sweet Charity, Donfeld for They Shoot Horses, Don’t They? and future Bob Mackie partner Ray Aghayan for a curiosity titled Gaily, Gaily, a coming-of-age farce that had nothing at all to do with being gay.

But looking at some of the more up-to-the-minute movies then reveals a banner year for costuming that foreshadowed the social progress and, not incidentally, major fashion trends seen in the decades that followed — and many that still endure today. Here are six fashion-forward films to consider.

  • Sweet Charity

    Bob Fosse’s first movie musical was a flop, but it’s a pretty good bet that designer Edith Head’s recreation of the spangly scanties worn by the Times Square dancers-for-hire would seemingly go on to inspire designer runways like Dolce & Gabbana and Peter Dundas in years to come (and were faultlessly recreated on the recent FX series Fosse/Verdon). But it’s Shirley MacLaine in her mini and fishnets who bravely decides to go it alone in the end and once again proves there’s nothing like the empowering virtues of a little black dress. 


  • They Shoot Horses, Don’t They?

    For his evocation of the hardscrabble dance marathons of 1932, designer Donfeld (whose versatile career would later include both 1987's Spaceballs and the original Wonder Woman with Lynda Carter) crafted costumes that made a star out of Jane Fonda. He was also tasked with outfitting the 350 to 700 extras in the film, and he reportedly kept 20 tailors and a hundred seamstresses hard at work in the process. Coming on the heels of 1967's Bonnie and Clyde, They Shoot Horses, Don’t They? ignited a wave a of '30s-influenced styles from '70s American designers such as Donald Brooks and Geoffrey Beene and heralded a new appreciation for bias cuts that extended all the way to later stars like Halston.

  • Easy Rider

    Peter Fonda and Dennis Hopper changed movies forever and “the hippies” even turned Hollywood currency upside down by reportedly recouping $60 million on a shoestring budget of $400,000. And Peter Fonda’s iconic Captain American jacket with the red, white and blue armband was the real thing, he told men’s magazine The Rake in 2016. It was tailored by “little old lady” Clarice Amberg of ABC Leathers in California, one of the first women to own a racing jacket company and known for injecting color into the usually black leather gear. “Dennis and I had our offices in Beverly Hills,” Fonda once said. “We were wearing our costumes to break them in, so the two of us were walking around looking like a couple of hippies. When we were on the street, people would run away from us!” Imagine.

  • Midnight Cowboy

    Joe Buck (Jon Voight) was the original urban cowboy and tight-fitting, vintage-style western wear has been a staple for a subset of fashion-conscious city slickers ever since. (Look no further than this week’s online The Journal from retailer Mr Porter, spotlighting London fashion editor Luke Day in his regular uniform of cowboy hat, tight western shirt, flared jeans and beat-up boots.) But Ratso Rizzo’s attire has turned out to be just as trend-worthy. Costuming legend Ann Roth said she scouted Dustin Hoffman’s costumes from Manhattan’s 42nd Street and bought his trousers from a table in front of the Port Authority bus terminal “for five bucks each with a dirty ridge where they’d been folded.” These days, though, fold marks are an ironic designer detail, seen from retro-inspired brands such as Gucci.

  • Bob & Carol & Ted & Alice

    Enormously popular — the fifth-highest-grossing film of 1969 — Bob & Carol & Ted & Alice reads like a time capsule of late-'60s Los Angeles style, from Dyan Cannon’s palazzo pants to Bob Culp’s love beads and bomber jacket to Natalie Wood’s paisley bikini. The critics loved the story of these would-be swingers, too, with scribe Pauline Kael of The New Yorker lauding director Paul Mazursky for his improvisational style, calling the effort "a slick, whorey movie, and the liveliest American comedy so far this year.”

  • Downhill Racer

    Though Robert Redford also starred in 1969’s top-grossing Butch Cassidy and the Sundance Kid, it’s Downhill Racer’s clean, sporty, post-preppie style that would seem a template for American designers who were just getting started around that time, such as Ralph Lauren and Calvin Klein. Not to mention those eternal tortoise-rim aviators. “You could stick the same clothes on, say, Bradley Cooper today and they would still look super-chic and stylish,” says Hollywood fashion consultant (and THR men’s style contributor) Andrew Weitz.