Beauty & Fashion · 27 March 2025
Oscars Fashion Flashback!
By Jo Casamento
The Oscars is technically a classy event, but let's be real — sometimes the red carpet is less "Old Hollywood" and more "oh my god, what were they thinking?!" And that's what we LIVE for!
Cher in 1986? She said, "Forget the dress, just glue some sequins to me and give me a headdress bigger than my confidence!" And let's be honest, she owned it in that Bob Mackie number.
Lizzy Gardiner in 1995 was a literal walking Amex ad! Her gown made of credit cards didn't make the best-dressed lists, but she had the last laugh — because nothing says "Best Costume Design" like "declined at checkout."
And Björk in 2001? Listen, fashion is subjective, but when you show up dressed like a Christmas dinner, you know you're serving. Iconic? Yes. Confusing? Absolutely. Still a moment? Always. Céline Dion in 1999 gave us "business in the front, party in the back" — literally. A backwards suit, with a fedora.
Suiting up in style
Billy Porter wearing a velvet tuxedo gown in 2019 was a game changer — the moment men everywhere were given permission to get creative. And Timothée Chalamet in 2022? No shirt, just vibes. That man showed up in a sequinned Louis Vuitton suit and became the pin-up for Gen Z.
Luxury labels? Not always!
Who needs a $20,000 gown when you can pop into a Gap store on the way to the Oscars? Sharon Stone's 1998 "business on the top, couture on the bottom" moment was so ahead of its time, people gasped like she'd walked in wearing a tracksuit. Fast-forward to Zendaya in 2022 — she took that exact formula and made it look so chic that designers were probably crying in their ateliers. It's the fashion equivalent of "I woke up like this," and they both make it so effortlessly glamorous.
Demi Moore's 1989 DIY moment
Are those bike shorts? Demi Moore is having an iconic fashion moment as she sweeps the awards season — but back in 1989 she single-handedly invented athleisure before it was a thing. Why wear a ballgown when you can throw on cycling shorts, a corset and some fabric you have lying around? It's giving DIY fabulous, and somehow… it kinda worked? Her and Bruce together… awwww.
Angelina Jolie's 2012 leg pop
Ah, the leg pop that stopped the world. Angelina Jolie stepped onto the Oscars red carpet in 2012 and the internet lost its mind. That slit was so dramatic and her leg pose so weird, it got its own fanbase. The memes? OUT OF CONTROL. You know you've made history when your limb goes viral.
My 2025 red carpet predictions
THIS is the million-dollar question! Here's what I'm expecting to see:
Old Hollywood glam — structured silhouettes, dramatic gloves and hair that says "I belong in a black-and-white film."
Futuristic metallics — space-age chic, like "I just stepped off a spaceship, but make it couture."
Barely-there fashion — sheer everything, daring cut-outs, and silhouettes that make stylists very nervous.
Bold menswear — more men ditching the traditional tux for experimental looks. (Timothée, I'm looking at you!)
And of course, something completely unhinged that we'll be talking about for years. Because what's the Oscars without a little red carpet chaos?
