Not Another 'Best Dressed' Oscars Post—I Swear
The Oscar Goes To These 'Mic-drop' Moments.
The Oscars have, and will always be, Hollywood and fashion's night of nights. Even when television’s night of nights sets up camp on YouTube. And so it goes that every year, the fashion media goes into [now AI-assisted] overdrive to bring you their take on who wore what and who wore it best.
But after decades in the editor’s chair, I can testify that the real stories don’t happen on the red carpet or "best-dressed" lists. Oscar 2026 wasn't just about Grace Kelly-inspired Chanel couture (I bow down, Jessie), Gucci feathers (Demi bringing her fashion game at 63), or the return of the ‘revenge dress’ (Nicole Kidman, we see you).
At The New Front Row, the promise is ‘Style, Storytelling and The Sh*it We Should Be Talking About’—and the Oscar goes to…
Jessie Buckley: ‘The Mother Of All Speeches’
The night belonged to Jessie Buckley, who rightfully took home the Oscar for Best Actress (for her career-defining turn as Agnes Shakespeare in Hamnet). The Irish actress also secured first place on my unofficial best-dressed list. Channeling a modern-day Grace Kelly, Buckley stole the show with her chic sideswept champagne bob (nothing c*nty about it) and the custom Chanel bubblegum gown with an off-the-shoulder wrap neckline in contrasting red (Kelly wore a similar one to the Oscars in 1956).
But more importantly, Buckley won my heart.
Devoting her impassioned speech to “the beautiful chaos of a mother’s heart,” (weep) Buckley, who has an 8-month-old daughter along with an Oscar, said of her character, “to get to know this incandescent woman and journey to understand the capacity of a mother’s love is the greatest collision of my life.” And then there was the public display of adoration for her husband, Freddie Sorensen. “Fred, I love you, man. You are the most incredible dad, you’re my best friend, and I want to have 20,000 more babies with you!” It almost makes me believe in marriage again.
Rose Byrne: ‘The Aussie Connection’
My fellow countrywoman may not have taken home the gold for her raw, intense, career-defining performance in If I Had Legs I’d Kick You, but she was heavenly in a strapless black, floral-embroidered dress with a dramatic mermaid train. And hearing that thick Aussie accent as she rejoined the cast of Bridesmaids to present Best Original Screenplay was gold in itself. Speaking of gold, Byrne did pick up the Golden Globe for her portrayal of Linda, a psychotherapist pushed to her absolute breaking point in the movie, cementing her rightful place among Australia’s best actors—Nicole Kidman, Cate Blanchett, Hugh Jackman, Margot Robbie, and Heath Ledger.
Ironically, her breakout role was alongside Ledger in the 1999 crime/comedy Two Hands. BTW, if you're in NYC, make sure to check out its namesake café.
But I can’t even with this Facebook post by Hunters Hill High School, where Byrne attended: “Congratulations to former Hunters Hill High School student Rose Byrne for her Best Actress win at the Golden Globes. Rose has also been nominated for Best Actress at the upcoming Oscars. Good Luck Rose!”
Sean Penn: ‘The Iconic No Show’
What’s not to love about Sean Penn? The legend, now 65, took home the Oscar for Best Supporting Actor for his role as the ruthless Colonel Steven J. Lockjaw in One Battle After Another, for which he was a no-show (ditto when he won the Golden Globe). Penn’s been nominated for an Oscar six times (winning three), and while his MIA status on Hollywood’s biggest night was kind of epic, it wasn’t a diss.
Penn’s focus is currently on the front lines (not the red carpet). He was in Ukraine meeting with President Zelenskyy to continue his work with CORE (Community Organized Relief Effort), the crisis-response organization he founded. His activism has evolved from celebrity outreach to genuine, boots-on-the-ground logistics, providing everything from medical supplies to structural support in war zones. Sean, I salute you. You’re the only person in the world who can win an Oscar from a bunker.
Anna Wintour: ‘Fashion Is Art’
On planet fashion, Vogue is the Bible, and Anna is God. She is, after all, the real-life inspo behind The Devil Wears Prada. BTW: for all you fashion-obsessed cool girls, the long-awaited sequel drops on May 1st. It’s kind of ironic that this year’s Met Gala exhibition is “Costume Art” (dress code: fashion is art) because here was Wintour, the accidental actor playing herself (or rather, the caricature of herself), while playing Oscar presenter.
For this long-time fashion editor, seeing Anna on that stage was the “lit”. It’s about time the queen of fashion had her proper Oscar moment. Rumors may continue to swirl that Wintour, now 76, is on the road to retirement after stepping down as EIC, but I don’t think she—or her signature black glasses—are going anywhere anytime soon.
Gwyneth & Demi: ‘Midlife Fashion Slay’
“Fashion is dead for women over 56,” according to The Telegraph. Kill me now. I’m not sure what bubble they live in, but I hope they tuned in to the Oscars to see a sea of 50-plus women killing it—Nicole Kidman, Gwyneth Paltrow, Demi Moore, Maya Rudolph, Kristen Wiig, Melissa McCarthy, and Sigourney Weaver (76 thank you very much). So to hell with that outdated and obnoxious fashion theory.
For my money, Gwyneth proved why she’ll always reign as queen of old-Hollywood royalty, looking decades younger (not that she needs to, but she does) with her immaculate complexion, sleek sidepart (many stars greenlit its return), and “naked-but-not-really-naked” strapless ivory silk column Armani Privé dress. Talk nailing the naked trend in real life and midlife.
And LFG Demi Moore, who has found her fashion and career stride in her 40s, 50s, and now 60s (as I wrote about for The Fashion Times). In a world of safe fashion, be a Demi, who crushed it in a custom emerald green Gucci gown dripping in peacock-style feathers and a dramatic black train.
At 63, no less.
Nicole Kidman: ‘The Quiet Revenge Tour’
Nic (as she’s affectionately known in our native Aus) continues on her “Keith Who?” “F You” revenge tour, which she’s done quietly and delicately, especially last night in an ethereal powder pink silk dress with a crystal-encrusted bustier and a peplum waist that cascaded onto the skirt in beige, pink, nude, and apricot feathers. Slay.
If the dress spoke volumes, so did her turn as presenter. Kidman dialed up the sex siren act as she flirted with Ewan McGregor to present Best Picture in honor of the 25th anniversary of Moulin Rouge!. When the two burst into “All You Need Is Love” lyrics, it was the dopamine high every divorcée needed.
Jacob Elordi: ‘The Date Heard ‘Round The World’
It was certainly a night for the Aussies, but the Oscar for “Son of the Century” goes to Jacob Elordi. Nominated for Best Actor, Elordi—who spent over 400 hours in the makeup chair to transform into Frankenstein—won hearts for taking his mum, Melissa Elordi (54), as his Oscars date.
The handsome-as-hell Brisbane-born actor, 28, promised her when he was 15 that if he ever made it to the Academy Awards, she’d be by his side. As a boy mum, I can’t even imagine how Melissa must have felt, but the images of them on the red carpet—and her emotional Instagram post—say it all.
Javier Bardem: ‘No War For Hot Men’
Speaking of being a boy mom, my youngest is Javier. He’s not actually named after Javier Bardem, despite my having a crush on him since forever—I mean, when he played the chilling, bowl-cut assassin in No Country for Old Men, I was gone. No, my Javier was actually named after a random guy I met at a dance party on a beach in Spain a million moons ago.
But here’s why Javier (both of them) will always be my guy.
Politics entered the Oscars chat—despite every A-lister being warned to “keep politics out their fucking mouths”—courtesy of Javier’s pin. Buttoned to his suit, the pin read in Spanish “No a la guerra” (No to war), and the actor used his moment at the podium while presenting Best International Feature Film to utter a clear, firm “Free Palestine.” There’s definitely something about the men from Spain.
Michael B. Jordan: ‘The Fashion Flex’
The actor took out Best Actor, a win the rumor mill insists was stolen from Timothée Chalamet after “Ballet-and-Opera-Gate”. I don’t buy the robbery narrative because Michael was sublime playing identical twin brothers in Sinners. He also takes gold for his best-dressed fit—a custom all-black Louis Vuitton ensemble by Pharrell featuring a sharp military-style high collar and a sleek chain detail. A best dressed award approved by my stylish son, Javier, the 14-year-old up-and-coming influencer/fashion model, giving young dudes the green light to dress well. I mean, give him Michael B. Jordan and Pharrell all day, every day.
Jordan is only the sixth Black man to have ever won Best Actor, and he called out the giants who paved the way—Sidney Poitier, Denzel Washington, Jamie Foxx, Forest Whitaker, and Will Smith (even despite the slap). He also honored the real heroes in his story: his father, Michael A. Jordan, who flew in from Ghana, and his mother, Donna, also his date for the night. Aww, these boys. But perhaps the best bit? The actor celebrated the old-school Hollywood way: hitting up In-N-Out Burger, still wearing “that suit,” and placing his newly minted statue on the counter while he ordered. Flex.
Jimmy Kimmel: ‘The Comedic Resistance’
In a sanitized political Oscars, kudos must go to this comedic duo for the digs heard ‘around the world’. In a short segment, Jimmy Kimmel didn’t hold back regarding freedom of speech. “There are some countries whose leaders don’t support free speech. I’m not at liberty to say which. Let’s just leave it at North Korea and CBS.” Then on the subject of documentaries: “There’s an international community of filmmakers dedicated to telling the truth, oftentimes at great risk to make films that teach us, that call out injustice, that inspire us to take action, and there are also documentaries where you walk around the White House trying on shoes.”
Gloves off.
Next came O’Brien’s quote of all quotes as he returned after a break. “Welcome back to the ‘Has A Small Penis Theater’—let’s see him try to put his name on the front of that one,” in response to the outrage around the renaming of the Kennedy Center by you know who.
Conan O’Brien: ‘The Host For Life?’
Hosting the Oscars is an honor that can make or break your career. The jury is out on Conan re-hosting—what were your thoughts? Clearly, the Academy was pleased, and that’s all that matters.
In pure cinematic gold, the final scene/skit sees Academy officials tell Conan he’s the permanent host and lead him to a plush new “Host for Life” office. O’Brien is locked in his new room with a view, gassed through the vents, and his body is unceremoniously dumped down a garbage chute. Sound familiar? Let’s just say Sean would have been proud.
If only he’d turned up.
Cassandra Kulukudis: ‘One Battle Finally Won’
And finally, for the first time in Oscar history, an award was introduced for Best Casting. Unbelievably, its inclusion has been the subject of fierce debate, with purists arguing it “clutters” the telecast. Incidentally, the inaugural award went to Cassandra Kulukundis for her work on One Battle After Another. She was the one who assembled the massive, high-stakes ensemble—hello Leonardo DiCaprio, Sean Penn, Benicio del Toro, and Regina Hall. Not to mention Chase Infiniti, the 25-year-old, ‘completely unknown no more’ breakout discovery of the film.
Let’s be clear: casting directors are the ones who source and recruit the talent that catapults these stars and their movies to Oscar glory. Just like a top-tier recruitment agent, ensuring the best hire lands the job to guarantee a company’s success.
Put through an Aussie lens, an Oscars ceremony without a casting category is like a pub with no beer.
That’s a wrap.