40+ of the Best and Worst Oscar Dresses of All Time

The brunette beauty wore a classic-looking satin halter dress designed by Marc Bouwer. While not over-the-top, its sultry subduedness made it stand out among the rest on that night. The creamy white of the satin shone against Angelina’s tan skin, and the whole look gave us Marilyn Monroe vibes.

Some have declared this dress an Oscar winner, and it absolutely qualifies to be on this list! Angie definitely knows how to put her best look forward.

One of the world’s most adored actresses, Audrey Hepburn, never failed to make her mark wherever she went. Back in the early days of the Oscars, the ceremony wasn’t the pomp and ceremony it is today, and cocktail dresses were the norm. Audrey, winning Best Actress for Roman Holiday, looks positively stunning in this white Givenchy dress.

It’s no wonder she wore a Givenchy design, as she was great friends with Hubert de Givenchy. The unique boat neckline showed off Audrey’s slim neck and perfect posture, and that style wasn’t common for such an occasion. It’s no wonder it’s been a celebrated Oscar design since then.

Well, what can we say here? It makes a statement, that’s for sure! The Icelandic singer was covered in feathery tulle and a swan’s neck draped around her neck, ending with its head strategically covering her chest. Not only did she wear this dress, but she, um, laid eggs walking down the red carpet!

Although this dress was (and still is) certainly capturing negative attention at the time, we have to conclude that it’s become iconic all these decades later.

No stranger to red carpets, this Welsh actress walked away with the Best Supporting Actress for her role in Chicago. At the time, Catherine was heavily pregnant with her daughter, Carys, but Versace came through for her and created a stunning gown in an unusual yet complimentary color.

We can’t imagine being all dressed up and having to sit through an entire Oscar ceremony as it is, but being nine months pregnant as well?! At least the dress looked comfortable!

Charlize usually hits all the right notes when attending red-carpet events, yet she missed one here in 2010. The color of the gown is gorgeous, but what on Earth are those things on her chest?

They just call ALL the attention, don’t they?! The Dior spokeswoman just left us with gaping mouths. We all make mistakes, Charlize, so don’t feel too bad. At least this dress shows off her stunning figure.

Ah, Cher, always putting a toe over the line and making us gasp. While Cher has some memorable Oscar outfits, and there’s always another one coming up, this one makes us wonder what she was thinking. Didn’t she get the memo that the Academy Awards required formal attire, not beachwear?

While we commend Cher for being different, sometimes it can be too much. Then again, Cher likes that this part of her personality brings her attention – negative attention included.

The supermodel looked heavenly in this white bandage dress from designer Herve Leger. It’s a simple style that showed off her model figure. Embellished with a simple updo and sparkly diamonds, Richard Gere’s date was stunning.

She had everyone looking her way. Being in the fashion world, Cindy is sure to know the right outfit to wear to a red carpet event.

What an absolutely stunning dress, so perfect for the Oscars! The Versace design is adorned with sparkle, so Elizabeth didn’t need to add much jewelry apart from a bracelet and some earrings.

Even her matching purse was bedazzled! Elizabeth has an eye for couture and this one, although not her most iconic look, is one of her best looks ever!

Sometimes, simple is the best way to go. This simple, baby-pink Ralph Lauren design made sure the night’s Oscar winner went down in the memory books. Gwyneth paired the dress with an equally simple slicked-back hairstyle and choker.

Yes, most of us remember her tearful acceptance speech, but at least she looked adorable! Gwyneth has gone on to say she’s kept most of her Oscar dresses for her daughter one day. We’re sure Apple will pick this stunner!

Who on Earth comes up with some of these designs? Oh, it was Demi herself. Well, this proves that some things should absolutely be left to professionals. Who in their right mind would wear cycling shorts to the Academy Awards? There we said it; Demi was clearly not in her right mind.

And that lining on the skirt bit just reminds us of Grandma’s curtains. Demi, you’re a gorgeous woman! Go and have a cup of coffee with a designer and give them your ideas next time.

This Ellie Saab creation wowed us then and still wows us now! Halle Berry went on to win Best Actress for her role in Monsters Ball, and what a dress to accept such a prestigious award in!

From the color to the delicate strategic embroidery, this dress will always be on the best-dressed list. We wonder if she still has it in her closet.

Edy Williams always broke the rules when it came to attire for the Academy Awards. Although this one wasn’t as revealing as the ones she’s worn in the past, it screams more figure skater than red carpet.

You can’t fault her toned body, but this dress just doesn’t suit her. They do say you should dress your age, and although we don’t want to be ageist, we do think perhaps this dress was too young for her.

Hilary may have won the Oscar that night, but this dress just made the win all that much sweeter! As she was walking up to the red carpet, you would never have guessed the dress was backless until Hilary turned around. And what a back!

This dress was perfect for showing off the actress’ lithe figure. Guy Laroche designed an immaculate outfit for an incredibly talented actress. The color, the material, everything just works!

Who doesn’t love rainbows? We love rainbows, especially after rain. But we love them in the sky, not so much on our bodies. The style of Faith’s dress is gorgeous and fits the stunning country singer well; we just don’t agree with the colors at all.

Let’s keep the rainbows in the sky and your songs, Faith. We’re confident you’ll get it right next time.

Who can forget the night when JLaw won Best Actress for Silver Linings Playbook? We know she can’t, and it’s because of this dress. The Dior Haute Couture dress got tangled up while she was walking up the steps, and she fell. Poor thing! But she handled it with all the grace and style that we know her for.

Jennifer let the dress do all the talking on the red carpet, as she only paired it with a very delicate necklace, earrings, and subtle makeup. It’s a very simple princess dress that allowed her to be a well-deserving princess for the night.

Geena was nominated for her role in the iconic Thelma and Louise. It’s a pity her dress wasn’t as iconic as her movie, though. This design by Ruth Meyers and Bill Hargate looks more like a frothy milkshake than a dress worthy of an Oscar nominee.

At least Geena has legs that can be shown off. But what are those ruffles at the bottom of the dress? Fashion sure was different in the early ’90s!

Not everyone can pull off a mint green dress, but JLo certainly can! From the one-shouldered overlay to the intricate embroidery, everything about this Valentino dress is perfect.

Jennifer’s flawless skin just glows with this color. Elaborate earrings, a simple bangle, and subdued makeup all make this look an absolute classic.

While we applaud anyone wearing a dress with pockets, this dress just… well, failed. Oscar de la Renta, we’re declaring our disappointment. The color looks amazing on Jen, but the style just doesn’t fit well. And what on Earth is that jacket doing? It doesn’t work!

It was said afterward that Jen did have another dress in the pipeline but was coerced into wearing this sad creation. What an absolute pity. Hopefully, the backlash made the person rethink their stance on forcing people to wear something they don’t want to wear.

Old-school Hollywood glamor is never a bad thing, and Jessica shines in this Armani Prive gown. The geometric patterns just enhance the already stunning shape of the dress and highlight Jessica’s slim figure.

The gold color compliments Jessica’s porcelain skin, and the lack of jewelry isn’t missed as she didn’t need any more than what she had. Her simple hairstyle is a perfect addition to round off this gorgeous outfit.

We love us some Kate Hudson, just not in this hodge-podge of eras. The dress’s neckline/collar and the hairstyle both look Victorian, while the rest of the dress looks modern. And the color?

The color is too drab for gorgeous Kate and definitely too dull for the Oscars. While Kate has gone on to declare that she loves this dress and still has it in her closet, sadly, no one shares her opinion.

The Erin Brockovich star collected her statuette in a Valentino design that she chose the week of the award ceremony. Talk about cutting it close!

The black floor-length gown had cleverly designed white piping up the front which formed a Y into the straps. This dress has often been referred to as an iconic Oscar gown, and we agree! Valentino has stated that seeing his design on the big Oscar stage was one of his proudest moments.

Here we have another actress who thought she could have a go at designing. Kim, honey, you either have the talent or you don’t, and we’re here to ask you to please stick to what you’re good at – acting.

This outfit looks like it can’t make up its mind. Is it a suit? Or is it a dress? We just don’t know, and our confusion is distracting us from the awards.

Um, we honestly don’t know what to say here. The only thing that comes to mind is a frilly sea slug. We’re truly looking for some positives about this dress and coming up empty. It’s just ghastly!

Kristen is such a lovely woman, but this doesn’t do her any favors. Not only is the dress weird but why is she wearing black gloves with it? Everything about this outfit is just wrong!

Black has always been a staple for elegance, and this Alexander McQueen creation screams elegance. Although we’re not too sure what’s going on with the hips, at least Lady Gaga can strike a pose with them!

The whole outfit was a tribute to Audrey Hepburn’s Breakfast at Tiffany’s look, including the huge diamond around Gaga’s neck. The very same stone was worn by Audrey back when she did publicity photos for the movie.

This ethereal dress was made for Lupita by Prada, and the color is absolutely breathtaking on the actress. This was her first Oscar ceremony, and she was nominated for her role in 12 Years a Slave.

She chose the color because it reminded her of her home in Kenya. We’re sure it brought her luck because she went on to win the Best Supporting Actress statuette.

Linda didn’t get the memo that shag carpets went out of style in the ’70s. This fluffy mess might be a pretty color, but it’s not a pretty dress for any event.

You’re a talented actress, Linda, but be sure to get on board with a proper wardrobe stylist next time.

This is an unusual color to wear on the red carpet, but Oscar-winner Michelle slays in this gorgeous dress. Nominated for her role in Brokeback Mountain, Michelle wowed in this Vera Wang gown, which was a throwback to vintage Hollywood.

Coupled with a simple bun in her hair, red lips, and a tiny clutch, this outfit is sure to go down in history as one of the best Oscar looks.

Yes, the Oscars are all about golden this and that, but credit cards? Hmmm, how very odd. Odd, but certainly memorable. Lizzie won an Oscar for costume design on the movie Priscilla, Queen of the Desert, but somehow didn’t get it right for the red carpet.

Don’t get us wrong, this dress is unique. But how on Earth did she handle the evening in it? How did she sit? How did she go to the bathroom? Enquiring minds want to know!

The Hannah Montana star walked the red carpet in this Zuhair Murad creation and received lots of praise. The layered scales on the skirt remind us of a mermaid, and the shell-like design on the belt with accompanying pearl seals the deal.

Miley grew up before our eyes, and when we saw her in this absolute stunner of a dress, we knew we were old! What a stunning dress for such a stunning young lady!

Again, we’re reminded that sometimes you’re supposed to dress your age. Unfortunately, Sally didn’t get that message. Whatever she was trying to wear here fell short. Are those supposed to be butterfly wings?

Your guess is as good as ours! We’re all for letting it all hang out if you can flaunt it, but if you can’t, have some self-respect and cover it up.

Statuesque Nicole looks ravishing in this John Galliano-designed Christian Dior gown. The color is flawless on her and it complements her skin tone perfectly. If you didn’t notice, the neckline was influenced by another dress on this list, namely Audrey Hepburn’s 1953 Oscar dress.

Her ex-husband, Tom Cruise was up for an Oscar that night, but everyone’s attention was on his arm candy in this uniquely gorgeous dress.

Supermodels getting it wrong seems to happen a lot but, thankfully, not too often. Sadly, Tyra Banks banked too much on this lilac number and came up short.

The tulle skirt looks like an afterthought and doesn’t match the material used for the bodice. Not everyone is perfect, we get it, but we didn’t expect Tyra and designer Vera Wang to fail so badly.

This Atelier Versace dress with a patterned bodice that opens into a flowing feathered skirt is outstanding! Penelope is glowing with colors that compliment her flawless skin.

Rounding the look out with an elegant updo, simple earrings, and a bracelet, the Oscar nominee looks radiant on the red carpet.

Exactly what is going on with this outfit? There’s so much tulle! And is that an attempt at a waistcoat? Nothing seems to match, neither color nor style. If we’re not mistaken, Uma doesn’t look all that comfortable or confident in this dress either. We don’t blame her!

Even though Uma picked it up off the Christian Lacroix runway for the Oscars, we’re sure she’s sorry she did. Perhaps this is a case of trying too hard to be different.

Sandra channeled the Oscar statue itself with this metallic silvery-gold dress with lace overlay. It proved to be her good luck charm as she won the coveted award that night for her role in The Blind Side.

Pairing the dress with a delicate bracelet, matching clutch, simple earrings, and her lovely brunette locks down, Sandra was a winner on the fashion front too.

This controversial comedian and talk show cohost didn’t seem to have a clue what to wear to the 65th Academy Awards. While the jumpsuit is rather flamboyant, it’s the eye-watering lime green lining of the skirt that has us cringing.

There’s so much going on here that we just need to say that simple is always better. This outfit is just too much in every aspect.

Ending off our list with a good one, Taraji is oozing glamor in this custom Vera Wang creation. With the keyhole neckline and alluring yet understated slit, Taraji is radiant at the 90th Academy Awards.

This just goes to show that you can absolutely wear tulle and not have it all be see-through. It’s always a good thing to leave things to the imagination.

Yes, yes, we just said Angie knows how to put her best look forward. Yet, here we are, in 2012, with her actually putting her best LEG forward. Angie, darling, what was going on this night?! Why is your LEG the star of the show?! This Oscar look has been memed into eternity!

While the dress itself wasn’t terrible, it was the alluring slit and what Angie kept doing with said slit and her leg that made this such a memorably bad outfit. That pose will never be forgotten! We’re sure she’s learned a thing or two about dresses and slits by now.

And here, Charlize makes the nice list! This was her night, as she walked off with the Best Actress Oscar for her role in Monster. It’s amazing to think that here she is in this stunning sparkly Gucci dress, showing off her slim figure, yet for the role, she had to gain 30 lbs!

The dress had embellishments of crystals, and the tan color complimented her skin. Did you know she even had to be sewn into the dress?

Designer Bob Mackie certainly created a one-of-a-kind dress this time around. Cher’s designer of choice wanted to make sure she’d win her Oscar in her own special style, and he succeeded. Although Cher won Best Actress for her role in Moonstruck, how many more people remember the dress rather than the award?

We gotta hand it to Cher, though; she’s got guts! And with a body like hers, who wouldn’t want to show it off?! We just have to know, was she able to wear any underwear?

Sometimes, even supermodels get it wrong. The model with the mole sadly chose an ill-fitting dress to attend the Oscars. The color suits her well, as does the bouncy hairdo, but the top half of this red sock (that’s what it looks like) just doesn’t fit right.

Thankfully, Cindy learned a few things and got it right a few years later with the white bandage dress.

Uh-oh! It seems our Oscar winner tried the daring route and failed miserably. This Alexander McQueen dress with a mesh top just raised eyebrows at the 74th Academy Awards.

Gwyneth is a gorgeous woman, and this goth look – whoever’s idea it was – just didn’t do her any favors. It’s since been revealed that she wished she wore a bra. We do too.

Everything is golden on Oscar night, right? So why not have a dress to match? JLo wins again with this incredible dress designed by Elie Saab.

The plunging neckline and exquisite beadwork are enough to make anyone feel like a princess in this dress. Jennifer’s simple ponytail and nude makeup make sure the dress is the star of the show.

Yes, Kate!! Coming back with a winner this time and a vintage-style Versace number, she glows on the red carpet! The plunging neckline and draped cape complement the whole outfit.

The accessories of a matching purse, some pretty sparkling bits, and the side-swept hair make for a memorable outfit well deserving of a place on the best-dressed list.

We know Stephani Germanotta likes to make a statement. Remember the meat dress? This monstrosity she wore to the 2015 Oscars has us wondering why she wanted to hide her lovely figure. It looks so heavy and must have been exhausting to wear for so long.

And what was she planning with those musketeer-style gloves? Did she sneak in some of her own snacks? Or maybe she tried to sneak some out?