Why These Iconic Oscar Dresses Hailed As The ‘Worst’ Were Actually The Very Best

Do you ever look at your back catalogue of bad boyfriends, and think with hindsight ‘maybe it wasn’t you, maybe it was’ – gulp – ‘me’? Mostly, no, I do not – I still think they are rogues and no-hopers (those being the censored versions of what I would really call them). But, in the spirit of honesty, well, yes there are a few who will forever be damned by my nearest and dearest that now make me think, ‘To be fair, I was a nightmare, I wouldn’t have wanted to date me either. Hope you’re well!’ (OK, I don’t really wish them well, but you get my point). The so-called ‘worst’ Oscars looks of all time, forever destined to be mocked and maligned, bring to mind those misunderstood boyfriends.

You know the ones. I’m talking about the back-to-front Dior tuxedo Celine Dion wore to the 1999 ceremony, the DIY cycling shorts get-up Demi Moore took for a spin in 1989, and Uma Thurman’s 2004 milkmaid Christian Lacroix look. And, of course, I’m talking about 2001 and Björk’s Marjan Pejowski swan – a look so iconic it is undoubtedly engraved on your memory.

Another woman springs to mind, and that's the one and only Cher, whose showgirl-esque outfit by Bob Mackie, which she wore as a presenter in 1986, has gone down in history as one of the most divisive of all time. Each of these ridiculed red carpet moments landed their wearers on the ‘worst dressed’ lists. But, in a reversal of how things usually play out, time has been kind to them. They have transformed from fail to fierce, from ugly ducklings to, well, swans. In 2024, they feel more relevant now than ever and deserve a second-chance.

In the last couple of years we've seen a revival of fun, joy, flamboyance and camp on the red carpet. Consider the rise and rise of Schiaparelli’s surrealism, Aubrey Plaza's meme-able Loewe post-it dress, Margot Robbie's monumental Barbie promo tour looks and each and every archive piece Zendaya has worn; now awards season belongs to those who don’t want to play it safe.

Besides, shouldn’t the Oscars be fun? And if they’re not, shouldn’t they at least be creative? This is when the highest echelons of Hollywood celebrate what they, one assumes, love to do: storytelling. In recent years, the red carpet has become a tautly choreographed step-and-repeat opportunity, one sculpted by commercial deals and impeccable stylists. But personal style and self-expression is full of so-called ‘mistakes’.

And that, years later, is the triumph of these looks: they expressed something about the person wearing them. They said something. Take Cher’s Bob Mackie look. The midriff-baring beaded two piece and extravagant feathered headpiece was seen as a playful two-fingers up to the Academy, who had failed to nominate her that year for her role in Mask. ‘Ha! Ha! Who cares? I'm Cher!’ she seemed to say.

Or what about the sheer Alexander McQueen dress Gwyneth Paltrow wore to the 2002 ceremony? Also widely mocked, but in hindsight A) a flash of nipple never hurt anyone and B) in its diametric departure from the pink Ralph Lauren gown she wore to collect her Best Actress Oscar in 1999, it took our perceptions of her from sweet to sexy and showed the world that she was not a one-trick thoroughbred. Many of these looks were simply ahead of their time. Now everyone’s doing cottagecore (like Thurman), deconstructed and directional tailoring (like Dion) and gloves (like Lady Gaga did in 2015).

In their refusal to play by the 'rules' these looks were the ultimate power move, worthy only of the kind of women so secure in their status and beauty that they don't care what anyone else thinks. Weird and wacky, ugly and unflattering? Bring it on. One must possess the confidence of the upper-A list, one-name-only brigade to pull them off. Kim Basinger and Demi Moore were so confident, they eschewed big name houses for their own design and styling talents, while Thurman has said she wore the Lacroix look because she was bored of seeing the same thing over and over on the red carpet. In other words, blending in is for B-listers.

Another thing all these looks had? Column inches. And since no publicity is bad publicity, I actually think the real ‘worst’ dresses are those completely nice-but-dull ones that showed no personality and which I will not list simply because I don't remember them and cannot be bothered to look at them again. You have to hand it to Cher and Björk and Demi and Gaga: they've still got us talking. Who’s laughing now?

So to the mistakes, the catastrophes, and, yes, even the swan, I say from the bottom of my heart: I’m sorry. It wasn’t you, it was us.