Oscars Red Carpet Fashion: Best Vintage Style Moments (PHOTOS)

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CHER
Cher at the Oscars. | Getty

If you thought we were going to cover vintage Golden Globe fashion and leave vintage Oscar fashion behind, you’ve got another thing coming. Why? Because some of us (hello) are obsessed with vintage fashion in general, and because the Oscars have consistently been the best annual fashion show since its 1927 creation.

So let us stroll down memory lane and celebrate the wonder that is classic, likely forgotten styles. And know that 50 years from now, this list will include Bjork’s swan dress.

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1. Who: Olivia De Havilland, 1950

Once upon a time, the Academy Awards weren’t the frenzy of red carpets and critics it is today. This explains Oscar winner Olivia De Havilland’s dressy, but not over-the-top choice. From the print on the skirt to the embellished short sleeves, the dress is fun and celebratory – not something it looks like stylists stressed out over in hopes of landing their client on the best-dressed list.

2. Who: Audrey Hepburn, 1954

Absolutely nobody reading this is shocked about Audrey Hepburn’s inclusion on our summary of vintage greatness. In her simple, pastel yellow tea dress, the Best Actress winner exuded style and grace – the adjectives she’s most synonymous with – and set the tone for the rest of her life. At only 25, she became a style icon . . . and acting icon, and human icon. Audrey Hepburn could really do no wrong.

3. Who: Grace Kelly, 1955

Grace Kelly is another one of those actresses who obviously understood her own style so well it just wasn’t fair to anybody else. Enter: the 1955 Academy Awards, and her green, ruched, satin number; complemented perfectly by her white gloves and embroidered clutch (the kind you can/will surprisingly find quite well at vintage and thrift stores today). Basically, thanks to choices like these, it’s safe to assume that for every year after, Grace Kelly earned a “best dressed” spot on any/all fashion round-ups. (Once they started, that is.)

4. Who: Ava Gardner, 1960

We’ve got a fur wrap, we’ve got white gloves, we’ve got a tiara, and we’ve got silver sequins. (Lots of them. Technically, we might even have all the silver sequins in the world.) This, friends, is true Hollywood glamour: a little over the top, a little controversial (a plunging neckline in 1960 would’ve been the stuff of conversation, absolutely), and something not all of us could carry off. Ava Gardner, we salute you.

5. Who: Barbra Streisand, 1968

Barbra Streisand has looked fantastic in everything she puts on since before we were born. Case in point: her flapper-esque shimmery Oscar gown, accompanied by a choker necklace and fantastic hair. This is the look of a woman who reflected the changing times: no more “feminine” silhouettes or traditional ‘50s glamour – with this Academy Awards look, Ms. Streisand represented how pop culture was about to get interesting.

5. b) Barbra Streisand bonus, 1969

See? A completely sheer pant suit and short, straight hair. Risks: the Barbra Streisand story.

6. Who: Raquel Welch, 1970

You say, “busy” or “too bright,” we say “the most magnificent gown in the world.” Why? Because we would never, ever see something like this today. The fear of placement on Fashion Police’s radar outranks the choice to experiment with colour, texture, and cut – which is a total shame, because Welch’s dress would earn accolades if we saw it on "Mad Men" or something.

7. Who: Jane Fonda, 1970

With a shag cut and minimal makeup, Jane Fonda exuded confidence and, well, awesomeness. But to top it off, she opted for a black dress and gold wrap, effectively keeping her look simple, but not boring. Arguably, she wore something any of us could easily wear today.

8. Who: Cher, 1973

Cher has more courage than any of us put together, and that is partially evidenced by her choice to wear a two-piece, midriff-baring ensemble to the 1973 Academy Awards (when we, probably, would just cover ourselves completely in Spanx). However, despite the obvious exhibitionism (and more power to her – this is a pro-Cher piece), it’s still a completely reasonable look: the long sleeves and skirt length balance the lack of mid-section fabric, and she inspires us all to do 100 sit-ups a day.

9. Who: Elizabeth Taylor, 1976

Elizabeth Taylor showed up looking like a million diamonds (see what we did there?) to nearly every Oscar ceremony, but there’s something about her ’76 choice that really drove home why her style remains so influential. In a strapless red gown and red chiffon wrap, she kept it minimalist – as she often did until the ‘80s – but still exuded the confidence and charisma that made her piece more than just a dress.

10. Who: Diane Keaton, 1976

Diane Keaton brought menswear into the forefront in "Annie Hall," so it’s understandable that she represented the look at the 1976 awards – a year before the film’s release. Of course, Diane Keaton has always been an actress who refuses to conform (at least in terms of fashion), so her choice to reject the conventional Oscar gown in favour the look she still gravitates towards is one that’s daring and rebellious. (Which, of course, is the best kind of choice.)

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