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The 20 best Oscar dresses from the last 20 years

Here are the top red carpet Oscars dresses from 1998 to 2018.
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There have been so many memorable Oscars gowns over the last two decades, but for a definitive list of the best, we called in the experts: The Fug Girls. Writers Heather Cocks and Jessica Morgan are the brains behind the beloved style website GoFugYourself, a go-to destination for smart, funny and often snarky commentary on celebrity fashion since 2004. Here, they share their picks for the top 20 Oscar dresses of the last 20 years.

Almost exactly 20 years ago, Nicole Kidman delivered a knockout punch at the Academy Awards by wearing a heart-stopping chartreuse Dior; on Feb. 23, she will step onto that same red carpet as one of the consistently biggest and boldest dressers in a styling game her gown helped change forever. Will Kidman come fashion full-circle with a nod to the dress that put her on the map? That question is just one of a zillion reasons we’re spending the Oscars glued to the fashion parade, awash in snacks and bubbly.

To whet your palette, we culled a list of our 19 favorite Oscar gowns since Kidman’s showstopper. Some you may have forgotten, some may be burned into your brains and — spoiler alert — some may involve waterfowl.

  • 1. Nicole Kidman in Dior, 1997

If you told us to close our eyes and imagine Nicole Kidman, two images would come to mind: a glorious mane of red curly hair and this photo. The dress was from John Galliano’s first Dior collection and, at the time, it felt wildly unusual for Hollywood’s big night. Even Tom Cruise is looking at her like he can hardly believe it, and he rode over in the limo with her.

Nicole Kidman in Dior at the 69th Annual Academy Awards
Nicole Kidman and then-husband Tom Cruise at the Oscars in 1997.Jim Smeal / Getty Images

This red carpet moment cemented Kidman as a style star and showed her fellow celebs just how gamechanging a well-chosen dress can be — after all, people can barely remember who won from year to year, but fashion can burn into their brains forever.

  • 2. Sharon Stone in Vera Wang ... and The Gap, 1998

Sharon Stone stunned everyone with this easy, breezy approach to what royal watchers now call “high fashion meets High Street" with her unexpected combo of a button-down Gap dress shirt and a Vera Wang skirt. Sure, the red carpet was less styled in the late ‘90s than it is these days, but most A-listers weren’t giving shoutouts to a mall chain, either.

Sharon Stone in Vera Wang and Gap at the Oscars
Sharon Stone wearing Vera Wang and a Gap shirt to the Oscars in 1998.Kevin Mazur / Getty Images

Best of all, Stone made us all feel better about those identical Gap staples hanging in our own closets (which may then have spawned a whole generation of hoarders, but hoarding is underrated anyway).

  • 3. Bjork in … a Swan, 2001

In the pantheon of crazy red carpet outfits, Bjork showing up at the Academy Awards wearing a bird has to rank among the absolute craziest. While this look is not wholly off-brand for Bjork as a human, it’s definitely, shall we say, unusual for the Oscars, where people don’t generally engage in interspecies cosplay.

Bjork wears a swan at the 73rd Annual Academy Awards
Bjork in her iconic swan dress in 2001.SGranitz / Getty Images

Even people who weren’t alive yet when this happened have somehow never forgotten it and, more importantly, Bjork and her swan dress have become an easy shorthand to explain why red carpet watching is such a delightful sport.

  • 4. Julia Roberts in Valentino, 2001

While this isn’t technically old enough to have been vintage, in that it dates from 1992, it did come straight from the Valentino archives rather than the runway — a thoroughly unexpected provenance. Its streamlined elegance is utterly timeless.

The 73rd Annual Academy Awards
An Oscar and a lovely vintage gown looked gorgeous on this "Pretty Woman."Terry McGinnis / WireImage

Valentino himself has said that watching Julia Roberts accept her best actress Oscar in this frock was the highlight of his career. It’s hard to argue with that; it was also possibly the highlight of hers.

  • 5. Kate Winslet in Ben de Lisi, 2002

Prediction: This dress will appear in every magazine spread that’s ever created about Kate Winslet’s career. The bold, red neck detailing capped a simple, curve-hugging sheath that should have taught the industry then and there that fashion isn’t just for the size 00s of the world. The designer, American-born Ben De Lisi, has lived in London since the ‘80s; Can we negotiate a knighthood, Your Majesty?

Kate Winslet in Ben de Lisi at the 74th Annual Academy Awards
Kate Winslet is the quintessential lady in red at the Oscars in 2002.Ron Galella / Getty Images
  • 6. Halle Berry in Elie Saab, 2002

Looking back at this dress, the sheer aspects seem almost played out. But at the time, this look was so fresh and unexpected — and Halle Berry looked so gorgeous in it during her tearful acceptance speech — that it felt quite revolutionary. It also launched Elie Saab as a major red carpet designer in the United States, a development for which we’re all grateful.

Halle Berry in Elie Saab at the 74th Annual Academy Awards
Halle Berry dazzled on the red carpet on what would be one of the biggest nights of her life.SGranitz / Getty Images
  • 7. Jennifer Lopez in Valentino, 2003

Why doesn’t J.Lo wear caftans more often? She looks awesome in them: floaty, glamorous and ever-so-Liz-Taylor inspired. (She wore this in the midst of Bennifer 1.0. Does that make Ben Affleck the Richard Burton of the early 2000s?)

Jennifer Lopez in Valentino at the 75th Annual Academy Awards
Jennifer Lopez looking elegant in a caftan in 2003.Frank Trapper / Getty Images
  • 8. Hilary Swank in Guy Laroche, 2005

Over the years, we’ve certainly seen plenty of prim-looking dresses with rear-view surprises, but none of them hit the mark as achingly well as this one. Just when you think maybe she’s wearing it backward, Hilary turns around, and boom. If we’d had Twitter in 2005, this would’ve been #BackGoals.

Hilary Swank in Guy Laroche at the 77th Annual Academy Awards - Arrivals
Hilary Swank had a surprise in store with her 1995 Oscars dress.SGranitz / Getty Images
  • 9. Michelle Williams in Vera Wang, 2006

Michelle Williams officially made it impossible for any other blonde — including herself — to wear a yellow gown and red lip without inviting comparisons. The rest will inevitably fall short, because this is flawless.

Michelle Williams in Vera Wang at the 78th Annual Academy Awards
Michelle Williams was quite the golden girl in her saffron Vera Wang gown in 2006.Frank Trapper / Getty Images
  • 10. Penelope Cruz in Versace, 2007

Penelope Cruz had been nominated this year for "Volver," making her the first Spanish actress ever to receive that honor (she would, the next year, become the first to win for "Vicky Cristina Barcelona"). In this dress, it hardly mattered whether she won; she was guaranteed to be the belle of the ball.

Penelope Cruz in Atelier Versace at the 79th Annual Academy Awards
Penelope Cruz defining red carpet glamour in her Versace gown in 2007.Frank Trapper / Getty Images

Do you even remember who did win this year? We had to look it up: It was Dame Helen Mirren. It speaks to the power of this gown that we completely forgot about our queen in "The Queen."

  • 11. Marion Cotillard in Jean Paul Gaultier, 2008

"La Vie en Rose" was America’s first real introduction to Marion Cotillard — and what a first impression. This gloriously detailed frock, including an almost tactile, scale-like pattern, took the concept of the mermaid dress to the next level.

Marion Cotillard in Jean Paul Gaultier at the 80th Annual Academy Awards
Marion Cotillard made a splash in this mermaid gown!Vince Bucci / Getty Images
  • 12. Viola Davis in Reem Acra, 2009

Viola Davis — nominated in 2009 for "Doubt" — is one of the red carpet’s most reliable women. She knows what looks good on her body and how to stretch those boundaries without going too far. It’s relaxing that we never need to worry about her. Having said that: This isn’t just good; it’s great. It’s a shame that no one ever rewears their Oscar dresses, because this one deserves a second turn.

Viola Davis in Reem Acra at the 81st Annual Academy Awards
Viola Davis at the Oscars in 2009. Practically perfect in every way.Frazer Harrison / Getty Images
  • 13. Cameron Diaz in Oscar de la Renta, 2010

Everyone in the background of this photo is gawking, which says something, because if you find yourself on the red carpet at the Oscars, you’ve definitely seen your share of up-close glamour before. Cameron Diaz wasn’t typically known for Old Hollywood glamour, so this was a heady, princess-y surprise. And one we’d love to see her re-create one of these days. Where are you, Cameron Diaz?

Cameron Diaz
There's something about Cameron Diaz ... in Oscar de la Renta in 2010.PAUL BUCK / EPA
  • 14. Amy Adams in L’Wren Scott, 2011

This was an “off” year for Amy Adams in the sense that she was between many of her nominations — yet she didn’t phone it in on the red carpet. In fact, she wore one of the sexiest and simplest sequined gowns we’ve ever seen on her, frosted with some beautiful emeralds (and, obviously, her entire enviable head). But this gown lives in our memories all the more bittersweet because of designer Scott’s tragic suicide in 2014. She was a force of creativity and elegance; what a light we lost.

Amy Adams in L'Wren Scott at the 83rd Annual Academy Awards
Amy Adams sparkles on the red carpet in 2011.Ethan Miller / Getty Images
  • 15. Jennifer Lawrence in Calvin Klein, 2011

Jennifer Lawrence’s first time at the Oscars — she was nominated as best actress for "Winter’s Bone" — was also her most successful, sartorially speaking. This tank dress put the exclamation point on her coming-out year by letting her playful, sporty aura shine through — not to mention, her bod. She set a high bar her first time out of the gate, but, luckily, she’s got a whole career ahead of her to top it.

Jennifer Lawrence in Calvin Klein at the 83rd Annual Academy Awards
The first (and arguably best) of J.Law's incredible Oscar gowns.Ethan Miller / Getty Images
  • 16. Gwyneth Paltrow in Tom Ford, 2012

She may not have succeeded in causing an uptick in genital steaming, nor consumption of grass-fed macrobiotic Himalayan yak milk, but the proliferation of red carpet capes? Gwyneth Paltrow can take some credit for that.

Gwyneth Paltrow in Tom Ford at the 84th Annual Academy Awards
While often associated with that pink gown from her Oscar-winning night, this 2012 Gwyneth gown takes the prize.Ethan Miller / Getty Images

She hasn’t been Oscar nominated since her surprise win in 1999, and while some people think that pink Ralph Lauren is her more iconic look, we believe this one is the more influential (and better-fitting). The second she strode onto the red carpet in this sleek gown, we knew it would spawn a passel of imitators.

  • 17. Octavia Spencer in Tadashi Shoji, 2012

Tadashi Shoji and Octavia Spencer are a great example of how the right marriage of actress and designer benefits both sides: Spencer glows, and because he made her look so unforgettable, Shoji becomes unforgettable, too. Even better: She won for "The Help" that night, so we assume this dress will live forever in a picture frame on her mantel, as it should.

Octavia Spencer in Tadashi Shoji at the 84th Annual Academy Awards
Octavia Spencer was pure elegance on the red carpet in 2012.Michael Buckner / Getty Images
  • 18. Jessica Chastain in Alexander McQueen, 2012

Why don’t more women opt for pattern on the red carpet? This lushly embroidered custom gown is regal perfection — a risk that paid major dividends. She’s never looked better.

Jessica Chastain in Alexander McQueen at the 84th Annual Academy Awards
Jessica Chastain looking gorgeous in gold embroidery in 2012.Michael Buckner / Getty Images
  • 19. Zoe Saldana in Alexis Mabille, 2013

Never has anyone thumbed their nose at the color wheel so effectively. Mabille is French, and this feels like a classic dish from his country: chock full of ingredients and requiring complex techniques, but in the end, somehow all you taste is the delectable whole. Pair that with Zoe’s inimitable panache and it’s a winner for the ages.

Zoe Saldana in Alexis Mabille at the 85th Annual Academy Awards
These subtle colors on Zoe Saldana's gown are simply lovely.Jason Merritt / Getty Images
  • 20. Lupita Nyong’o in Prada, 2014

Lupita collaborated with Prada to create this dress in a blue that the star said reminded her of Nairobi, where she grew up. It feels right that she wore a glorious Cinderella dress to cap off her own fairy-tale awards season.

Lupita Nyong'o in Prada at the 86th Annual Academy Awards
Princess Lupita!Jason Merritt / Getty Images

May we see many such joyous red carpet moments at this year's Oscars. (Although we’d accept more people in swan dresses, too.)

This story was originally published on Feb. 24, 2017.