The Coolest Looks From The Oscars Archive (That Don’t Get Shared Every Year)

We’re revisiting the Oscar archives: the B-sides and lesser-known hits from the Oscars vault.

As the red carpet gets steam cleaned for another year (in case you missed it, the 96th Academy Awards is taking place at LA’s Dolby Theatre on Monday) and Hollywood stylists race to secure the final touches for their clients, award show season gears up for the main event.

Fashion is part of the job for actors, and recent years have seen more acknowledgment of the work — and scores of people — involved in putting together a look for the red carpet.

These days the stakes are high, with multiple brand deals at play (including coveted jewellery contracts) and images widely distributed and picked apart thanks to online discourse and media appetite.

Pre-2000s however, it was a different case. The red carpet was still entertaining, but we saw less of it, limited to magazines and TV coverage, and public critique was limited to real-life conversations with your social circle.

Many celebrities dressed themselves; brands weren’t heavily invested in securing looks and leveraging events like the Academy Awards for brand marketing. People carried purses.

Costume designers were more commonly called upon than stylists. Often stars just bought a frock, or in the case of Sharon Stone, a Gap T-shirt.

So as we question the pace of the industry and the increasingly entertainment-focused approach of the fashion industry, here are some reminders of a simpler time.

Anjelica Huston

This ensemble (pictured above) is my favourite. Houston is pictured here with then-boyfriend Jack Nicholson, you should read her memoir for more on that relationship.

Cher

While it’s usually her outrageous Oscar-winning 1986 ensemble (Bob Mackie) or the sparkly and sheer 1988 look (also Bob Mackie) that make the lists, this breezy number is an underappreciated B-side. Weird, fun and sexy. Like a really trippy holiday. (And, you guessed it, Bob Mackie.)

Martha Plimpton

Attending the last Oscars of the 1980s, hand in hand with the late River Phoenix, Plimpton’s look is one I come back to every year. Glamour and grunge in equal measure. It’s vintage, of course, 1930s — just look at that bias — and apparently, she bought the dress the day of the ceremony.

Ingrid Bergman

A wide-shouldered sheath and some sensible sandals — this could be Prada now. Bergman won for Gaslight, and layered a coat (and large corsage) on after the ceremony.

Diane Keaton

Accepting the Oscar for Annie Hall, Keaton’s look has a distinctive air of la-dee-da. There’s care taken, and quality of course (it’s by Giorgio Armani) but a fussy gown this is not.

Miyoshi Umeki

In an era of full, frothy New-Look silhouettes, ivory tulle, and set hair waves, Umeki — the first Asian woman to win an Oscar — spoke volumes with her look, a classic kimono and blunt, straight fringe.

Anna Paquin

Still cool.

Whoopi Goldberg

Is the secret sunglasses? Maybe. But it’s more than that; it’s the pearls and the undulating velvet motifs on the silk; the great pumps and the dark lip.

Diana Ross

Playing with the tropes of gendered fashion on the red carpet is nothing new, as we see here with this swaggering, sensual three-piece suit on Diana Ross, complete with a cravat.

Faye Dunaway

There’s frou and then there’s Frou. If this was worn now, there would be a contractually obligated set of diamond jewellery. Instead, Dunaway has a purse that looks suspiciously functional. She was nominated for Bonnie and Clyde, and her look was created by the film’s costume designer Theadora Van Runkle.

Erykah Badu

A presenter at the 72nd Academy Awards, Badu incorporates elements rarely seen on the red carpet at the time. It was a breath of fresh air then, and remains so now.

Sharon Stone

Okay, this one gets shared a lot — after all, it’s the famous Gap shirt that made fashion history — but it’s still so cool. The story goes that the look was unplanned, with Stone turning to Basic Instinct designer Ellen Mirojnick for help after the Vera Wang gowns made for her didn’t pan out (Fortuny fabric can be temperamental, apparently). The best thing about this? As of 2022, Stone still had the T-shirt.

Bjork

Treated as a punchline at the time, Bjork’s infamous swan dress was an if-you-know-you-know choice (designed by Marjan Pejoski) and the look has come to enjoy renewed appreciation in the years since — now landing on “most iconic of all time” lists. With spectacle and safety the most common routes chosen by stars, this has true whimsy, joy and edge to it.

More fashion on screen

A round of applause for the costume department — we see you.

Dressing the high-society Swans in ‘Feud’ was an adventure in both authenticity and artistry. Feud: Capote vs. The Swans brings famous faces — and scandals — to life in a flourish of period-appropriate fashion.

How the costume designer for ‘The Panthers’ dressed a movement. The Panthers tells the story of the uprising among Pasifika people during the 1970s dawn raids in New Zealand.

The costume designer behind Netflix’s bingeable love story ‘One Day’ on the power of 90s style. Designer Emma Rees shares the nostalgic fashion trends she revived for the Netflix romcom One Day, from scrunchies to Levi’s 501s.

Unfurling the unusual costumes of ‘Poor Things’, a Victoriana fashion fantasia. The designer Holly Waddington breaks down how Emma Stone’s Bella Baxter evolves onscreen, from her childish knickers to her cage-like wedding dress.

‘Killers of the Flower Moon’ and Martin Scorsese’s bride like no other. The costumes of the epic drama have a storied history — and unparalleled wedding wear.