The most awfully memorable Oscar gowns of all time, from Demi Moore’s DIY disaster to Cameron Diaz’s floral fail | THE SUN

The most awfully memorable Oscar gowns of all time, from Demi Moore’s DIY disaster to Cameron Diaz’s floral fail | THE SUN

THE world will be watching as the 90th Academy Awards kicks off tomorrow evening.

While the golden statue is the ultimate prize, there’s something else that actors and actresses will be vying for – to be crowned best dressed.

Every year, fans are treated to an abundance of expensive, beautiful gowns – as well as their fair share of hideous, overly revealing and bizarre creations.While some choices leave us envious, others have us in stitches.

Money and fame certainly can’t always buy you style – and these memorable outfits are testament to it.

Demi Moore 1989

Demi’s DIY creation. Hopefully, other actresses will take note of Demi’s failed look: never try and make your own dress at home
Note to all: do not design and manufacture your own outfit. This is the result.
The bike shorts, corset feature and metallic floral-print fabric were all DIY Demi.
Just, no. Not even taking the handsome and very dapper Bruce Willis as your date makes up for this creation.
This is certainly top of Oscars “worst ever dressed” list.

Cameron Diaz 2002

Cameron Diaz had a shocker in this floral gown
We’re just not feeling this look on the usually flawless and radiant Cameron.

Floral prints are popular amongst fashion’s elite, however, it looks a little out of place here.

Cameron’s look is a little more sophisticated garden party rather than Oscars.

Plus, the belt, turquoise bracelet and brocade bag is just wrong on so many levels.

Gwyneth Paltrow 2002

This goth-like Alexander McQueen number appealed to no one, Gwyneth

It’s unlike Gwynnie to fall short of the Oscars best dressed list, yet in 2002 she did just that.

This goth-like Alexander McQueen number appealed to no one. The sheer bodice, heavy eye make-up and braids overall contributed to a memorable look for all the wrong reasons.

Thank goodness Gwynnie hasn’t repeated it since…

Susan Sarandon 1996

While tonal dressing is all the rage, please never match your hair to the dress like Susan Sarandon did in 1996

You can applaud Susan Sarandon’s couldn’t-care-less mentality when it comes to red carpet dressing, but this is one gown that isn’t worthy.


The fact that she matched her hair colour to her outfit is memorable enough.

Yet the heavy taffeta fabric just isn’t flattering and the veil she bought with it (not pictured) didn’t lend itself to “best dressed” appeal.

Anna Nicole Smith 1996

Anna Nicole Smiths 1996 outfit was a lesson in how not to dress
There’s a lot of things wrong about this dress.

Firstly, for anyone who is as busty as Anna was, please note that it’s important to stay far, far away from velvet.

The saccharine hue, smudged lippy and tacky brooch pushes this one to the top of the worst dressed list.

Simply, this look did nothing for the former Playboy star.

Cher 1998

Cher’s fashion choices leave a lot to be desired
Kudos to Cher, she’s not exactly concerned with what everyone else thinks of her sartorial choices (who could forget her 1986 Bob Mackie outfit?).

However, with this ensemble she falls spectacularly short.

The headpiece, hue and cut is more dire than “wow”.

Sorry Cher, but this dress doesn’t get our vote.

Celine Dion 1999

The backward blazer has only really be worn out in public once. The culprit? Celine Dion, alla 1999

 The backward blazer has only really be worn out in public once. The culprit? Celine Dion, alla 1999.

It’s refreshing to see an actress dispel the Cinderella-like dress in favour of tailored suiting.

Then again, when Celine Dion tried it in 1999, the overall effect was more odd than original.

We get it, it was the late 90s and individuality was all the rage. But this backwards blazer just isn’t doing it for anyone, Celine.

Angelina Jolie 2000

Morticia Adams? No, it’s actually Angelina Jolie. Bet you regretted this fashion choice Ange…

This goth-like creation would be more suited to Halloween than the Oscars.


Angeline Jolie channelled Morticia Adams in 2000, when she won a Best Actress Oscar for Girl, Interrupted.

It’s fair to say that she’s come a long way in the style stakes. Or, maybe not? Who could forget her assertive and provocative right leg in 2012…

Juliette Binoche 2001

Could someone please remind Juliette Binoche that the year is 2001, not 1921

It would seem that the French actress had confused 2001 for 1921.

This flapper number was the inspired creation of Jean-Paul Gaultier, but it was a bit more mishmashed than nostalgic.

The pearls, corset, gloves and hair clip is just all too much for everyone to take in.

Keep it sleek and simple next time, Juliette.

Faith Hill 2002

Faith Hill tries candy-coloured Versace. The result? Terrible

Candy-coloured hues can be difficult to wear. But, when you try to wear five variations of it you’re really in for trouble.

Faith Hill. Great singer. Terrible Versace dress.

Next time, leave the candy hues at home. Or just go for the one, not the whole rainbow.

Charlize Theron 2010

The swirled-bodice design is really unflattering, even on Charlize
Figuratively, this Dior number ticks all the fashion boxes. Logistically, it’s just plain bizarre.

Charlize Theron carries it well, but the swirled-bodice design is really unflattering.

Luckily, it was just a one-time fail for Charlize and Dior; their fashion partnership has certainly upped its game in recent years.

Heidi Klum 2016

Heidi Klum certainly turned heads in this lavender gown

This lavender chiffon number is not doing it for Heidi.

With huge gaudy flowers and a terrible awkward-cleavage cut-out, this was one of 2016’s biggest Oscars fashion faux pass.

The look was courtesy of Marchesa. We wouldn’t be surprised if this was the last time Heidi wore anything from that fashion house…

Kate Winslet 2016

This was a rather insipid fashion choice from Kate. She can definitely do better

This latex inspired number was just not a good look for the usually glorious Kate.

It had a rather unimaginative cut and bland style, which the actress accompanied with beachy waves and peach lipstick.

It’s not the most flattering dress Kate has ever worn. She can definitely can do better.

Scarlett Johansson 2017

The whimsical pink print and studded belt combo just isn’t working here

It’s not a bad dress. As you can tell from above, there’s been a lot of worse.

But the whimsical pink print and studded belt combo just isn’t working here.

It’s too informal and feels a little busy. Plus, the studded heels are utterly incongruous with the floaty, feminine design of the dress.

Better fashion luck this year, Scarlett.

This article first appeared on The Sun on 3/3/2018. Read it here: 



Catherine McMaster
Editor | Writer | Content Producer Editor - Sunseeker Magazine Editor - Gaggenau Magazine Editor - Unique Magazine Contributing Editor - THE SUN | NEWS UK

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