The Academy Awards were not always the pinnacle of high fashion that they are today.
In fact, the first year the awards were presented, Janet Gaynor went home with the 1929 Best Actress golden statuette wearing a simple sweater and skirt combo! Perfectly lovely, of course — but not nearly the luxurious gowns we’re used to seeing today.
Among the most notable mentions of the early years of the event, Audrey Hepburn set hearts fluttering in her sleeveless lace dress from Givenchy in 1954. One year later, soon-to-be real-life princess Grace Kelly was a dream come true in seafoam satin folds designed by Edith Head.
As the years went on, the prestige of the Oscars grew and the pressure was on every leading lady to look her very best. Looking like the queen of Hollywood she was, Elizabeth Taylor stole the show in 1970 swathed in — you guessed it — ruffle trimmed Edith Head, the gold standard for gowns of the time.
Half a decade later, all eyes were on Anjelica Huston in a stylish second skin of scales from Halston. Jack Nicholson on her arm didn’t make for a bad accessory.
Dressing in all gold is a longstanding tradition (and one that’s peaked in recent awards season especially). Farrah Fawcett perfected the look in ’78 with a molten spaghetti strap piece, topped off by her legendary waves.
Sharon Stone broke the mold in 1998, rolling up the sleeves of a menswear inspired white shirt and pairing it with a shimmering Vera Wang skirt of lilac satin. Not everyone was won over by the look, but it has claimed its place in Oscars history all the same.
Of course, nothing beats classic monochrome. Jaws dropped at the sight of Julia Roberts stepping out in her 2001 Valentino dress, which is so legendary it even has its own Wikipedia page now.
And no one has forgotten Angelina Jolie’s leg bomb at the 2012 Oscars, which goes down as one of the most memorable fashion moments in recent history thanks to her solid black Versace creation and its high side slit.
For fashion aficionados, the incident recalled another time when Angelina Jolie made headlines dressed in all black at the Oscars. Her goth-inspired 2000 ensemble was a sartorial highlight of the turn-of-the-millennium.
Though it shocked onlookers in 2001 and continues to attract its fair share of both admirers and detractors, no one will ever forget Björk’s “swan dress” designed by Marjan Pejoski.
Another dress that divided opinions was Marion Cotillard’s Jean Paul Gaultier gown of glittering scales. But whether you love it or hate it, the design incites strong opinions — and remains legendary for that reason.
There are a few Oscars darlings who earn accolades every time they step out on the red carpet, and Michelle Williams is one of them. The canary yellow Vera Wang confection she chose for 2006 is arguably her all-time best look.
In nearly a century of Oscars outfits, there have been a number of near-misses when it comes to fashion face offs. Take for instance Nicole Kidman and the cherry red Balenciaga halter neck dress she picked out in 2007, which was tied with a giant statement bow.
Fans had a delightful case of deja-vu five years later when Emma Stone appeared in a remarkably similar look from Giambattista Valli.
So what should you wear if you want to make an everlasting Oscars impression? History shows that maroon satin isn’t a bad choice. The Elie Saab gown Halle Berry wore in 2002 wowed crowds with its voluminous skirt and sheer bodice embroidered with delicate floral motifs.
Keira Knightly took a similar route in 2006, to much the same effect. Her one-shouldered Vera Wang mermaid gown is frequently cited as one of the best dresses not just from the Oscars, but of all time.
Or maybe the real key is not the maroon color, but the wrapped quality of the skirt? Jennifer Hudson’s bright orange Versace gown of 2011 was vibrant and vivacious, and its elegant folds made it a true work of art.
Though it’s mostly remembered as a scapegoat for causing Jennifer Lawrence’s fall at the 2013 awards, her Christian Dior Couture gown was absolutely incredible. Designed by Raf Simons, its creamy palette and statement proportions avoided wedding gown territory. Instead, it squarely hit the mark in terms of fairytale grandeur.
Is it just us or do the gowns keep getting more luxurious every year? There was Lupita Nyong’o’s Calvin Klein Collection dress of 6,000 pearls in 2015. Jennifer Lopez made every single best dressed list that same year in a nude Elie Saab masterpiece. Octavia Spencer, Charlize Theron, and Lady Gaga are among those who have made unbelievably opulent statements even more recently.
If the trend continues, we can safely look forward to unparalleled glamour at the Academy Awards this March 4, when Hollywood will mark 90 years of Oscars. Hopefully, nominees will do their homework and pull out all the stops with their ensembles, making Year 90 one to truly remember. — jas