Great Outfits in Fashion History: Winona Ryder's Frequently Re-Worn Armani Dress - Fashionista

Great Outfits in Fashion History: Winona Ryder's Frequently Re-Worn Armani Dress

She loved this dress so much that she wore it to the Oscars after she'd already been photographed in it at multiple Hollywood events.
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Winona Ryder in 1996 at the Artist's Rights Foundation Honors Martin Scorsese event in Century City, California.

Winona Ryder in 1996 at the Artist's Rights Foundation Honors Martin Scorsese event in Century City, California.

There are perfectly good celebrity style moments, and then there are the looks that really stick with you, the ones you try desperately to recreate at home. In 'Great Outfits in Fashion History,' Fashionista editors are revisiting their all-time favorite lewks.

In 2020, celebrities began making headlines for re-wearing their own clothes on the red carpet. Jane Fonda and Joaquin Phoenix both did so to make a statement about environmental degradation and over-consumption, and were praised by many slow fashion activists for their efforts. (Not to mention Tiffany Haddish's memorable turn with that white Alexander McQueen dress starting in 2017.) But the truth is that outfit repeaters are nothing new, even amongst the ranks of high-profile celebrities.

Case in point? Winona Ryder. Long hailed as a queen of '90s style, Ryder came to embody the decade's casual grunge with her concert T-shirts, worn-in jeans and leather jackets. What that translated to on the red carpet was a fair bit of gothic black, but there was perhaps no black ensemble Ryder loved more than her strapless Armani gown. 

A column dress that was fitted through the bodice before falling straight to the floor, the dress was rather simple. What made it special, though, was the unique neckline, which dipped elegantly in the front before curving up again at the side of the dress. 

Ryder loved the dress so much that she wore it to multiple high-profile Hollywood events. She paired it with a slick chignon, red lips and a bit of ear and wrist bling to an event honoring Martin Scorsese in 1996, then again later that year with her delightfully cropped hair to a cancer benefit (where she hung out with fellow '90s starlet Claire Danes, of course). Both times Ryder paired the dress with a simple black bag — a purse with a chain in one instance, a clutch in the other — and didn't overwhelm the minimalist design with much that could distract from it.

Winona Ryder arriving at the 72nd Annual Academy Awards in Los Angeles, California.

Winona Ryder arriving at the 72nd Annual Academy Awards in Los Angeles, California.

But the real proof that Ryder loved the dress came in 2000, when she opted to wear it again to the 72nd annual Academy Awards, aka the biggest event in Hollywood. This time she opted for more subdued makeup colors, and though the silk-lined shawl she carried would feel a bit out of place today, the satin headband she wore feels perfectly of-the-current-moment. (Prada's Spring 2019 runway, anyone?) Come to think of it, the dress itself looks like it could've been pulled off a contemporary runway, too – it might have been designed by Armani way back when, but we wouldn't be surprised to find a picture of Winona in it on the moodboard for Saint Laurent's Spring 2020 show.

All that's to say, if you're looking for inspiration to become more of an outfit repeater, just remember: Winona Forever.

And in case you're looking for an outfit of your own to wear to every fancy event for the next few decades, check out some of our favorite black pieces with memorable necklines in the gallery below.

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