Best Meta Moment

 

View this post on Instagram

 

A post shared by Just Jared (@justjared)

In promotion mode for The Devil Wears Prada sequel, Anna Wintour and Anne Hathaway presented the costume and hair and makeup categories. Wearing custom Christian Dior by Jonathan Anderson, Wintour channeled Miranda Priestly, played by Meryl Streep who famously channeled the Vogue head honcho’s, ahem, alleged management style in the original. Wintour’s “thank you Emily” to Anne Hathaway (who plays a beleaguered assistant) in Valentino Haute Couture by Alessandro Michele, was pure fashion froideur. Honourable Mention: Best I’m Ready for My Flowers Moment goes actress Rose Byrne, nominated for best actress for If I Had Legs I’d Kick You, who wore another custom Christian Dior gown by Anderson, considered one of his best of the season. 

 

View this post on Instagram

 

A post shared by Check The Tag (@checkthetag)

 

Best Wardrobe Malfunction in Waiting

 

View this post on Instagram

 

A post shared by Just Jared (@justjared)

The internet held its collective breath as Gwyneth Paltrow ran through the Oscar venue, strode the red carpet and walked onto the Oscar stage in a business-in-the-front, naked-on-the-sides custom silk Giorgio Armani Prive gown. While the comment sections seethed with thoughts on which, if any, parts of the actor were exposed, the brand clarified that “the dramatic cut-out sides revealed tulle nude trousers accented with subtle crystal embellishments.”

 

Best Sharon Stone Homage

 

View this post on Instagram

 

A post shared by Check The Tag (@checkthetag)

With temperatures on the Oscar red carpet hovering around 32°C, Pedro Pascal ditched the jacket and let his crisp white shirt show just how cool he is. While Sharon Stone’s 1998 look was from The Gap, Pascal was kitted out in Chanel by Matthieu Blazy, who showed white tuxedo shirts in collab with the French shirt maker Charvet for spring. Pascal’s exploded flower brooch in lieu of the brand’s trademark and restrained Camellia showed that the Lagerfeld era is well and truly over. Also part of the Blazy brigade: Maya Rudolph, Nicole Kidman and Teyana Taylor.

 

View this post on Instagram

 

A post shared by Check The Tag (@checkthetag)

 

View this post on Instagram

 

A post shared by Check The Tag (@checkthetag)

 

View this post on Instagram

 

A post shared by Check The Tag (@checkthetag)

Best “Who Wore It Best” Face Off

 

View this post on Instagram

 

A post shared by Just Jared (@justjared)

Heated Rivalry heartthrobs Connor Storrie in Saint Laurent and Hudson Williams in Balenciaga gave the people what they wanted in coordinating peek-a-boo tops of varying fluidity. Extravagant accents with tailored and tuxedoed pants finished this fashion win.

 

Best Can Con

 

View this post on Instagram

 

A post shared by Who What Wear (@whowhatwear)

Ontario’s very own and former model Paul Anthony Kelly reminded us exactly why he was cast as John F. Kennedy Jr. in the buzzy Ryan Murphy series Love Story. Further proof he is now on the fashion A-List? He was in a custom look from the 1 percent’s favourite brand, Brunello Cucinelli.

 

Best Movie Star Moment

 

View this post on Instagram

 

A post shared by Check The Tag (@checkthetag)

He invoked Sidney Poitier and Denzel Washington, among the seven black actors who have won in the lead categories since the Academy’s inception, and best actor winner Michael B. Jordan was as suave as those legendary lookers in his custom Louis Vuitton by Pharrell Nehru suit. The brooches gave it a global vibe but Jordan was all L.A., emoting on Leonardo DiCaprio’s welcoming shoulder, chest thumping from the stage to Friday Night Lights series co-star Jesse Plemmons and causing pandemonium at an In-N-Out Burger with Oscar in tow. In a related Best For The Culture Moment, Jordan’s Sinners director, Ryan Coogler, who won the Oscar for Best Original Screenplay, was resplendent in intricately patterned cornrows.

 

Best Winged Victory

 

View this post on Instagram

 

A post shared by Check The Tag (@checkthetag)

A year after she took anti-aging measures to the extreme, Demi Moore was leaning into her elevated old-crone era in a fully feathered Gucci gown by Demna that walked the line between macabre and magnificent. The witchy vibe was completed by her trademark swathe of black hair, released from the bob wig she sported at the Gucci show last month.

 

Best Retro Re-enactment

 

View this post on Instagram

 

A post shared by Who What Wear (@whowhatwear)

Best actress shoo-in Jessie Buckley, who swept the season for her role as Shakespeare’s wife and grieving mother in Hamnet, wore a revamp of a dress worn by Grace Kelly at the 1956 awards by iconic Hollywood costume designer Edith Head. The dress has lived on, seen in black and white images, but in Chanel’s hands Buckley joins the pantheon in technicolor.

Honourable Mention goes to Elle Fanning, a nominee for best supporting actress in Sentimental Value who gave a masterclass in the art of Old Hollywood Glamour in Givenchy by Sarah Burton.

 

View this post on Instagram

 

A post shared by Cosmopolitan (@cosmopolitan)

 

Best “Let Your Freak Flag Fly”

 

View this post on Instagram

 

A post shared by Check The Tag (@checkthetag)

Not satisfied with metamorphosing into The Fly in the ’80s, Jeff Goldblum and his Canadian wife Emilie Livingston wore one outfit and a fraction of another from ERL Artisanal, accented with ethically sourced, vintage upcycled skunk fur. Shrug Emoji.

 

Best Nepo-Babying

 

View this post on Instagram

 

A post shared by Just Jared (@justjared)

Kate Hudson’s comeback was crowned by her first Oscar nomination in 26 years as best actress for Song Sung Blue. Her sculptural Giorgio Armani Prive gown more than rose to the occasion while her mother, perennial it-girl Goldie Hawn, stayed perfectly on brand.

 

Best Rock Star Attitude

 

View this post on Instagram

 

A post shared by Check The Tag (@checkthetag)

Best supporting actress winner for her role in Weapons, Amy Madigan said “No” to the tyranny of the dress. As she did for the duration of the awards season, she looked cool and unbothered in novelty jackets from Dior, here paired again with a sharply tailored trouser that would make both Benny from the Jets and Sergeant Pepper proud.

 

Best “Don’t You Know There’s A War Out There” Look

 

View this post on Instagram

 

A post shared by Just Jared (@justjared)

Or did nominated Hamnet director Chloé Zhao go Sicilian widow meets goth goddess  because she agreed with Oscar host Conan O’Brien’s observation: “these are very chaotic, frightening times”? Or is it because her movie rests on the heartbreaking death of a cherubic child? Either way, designer Gabriela Hearst understood the assignment.

 

Best “I’ve Seen The Dystopian Future” Look

 

View this post on Instagram

 

A post shared by Just Jared (@justjared)

In the face of AI, convergence and the other market forces that puts Hollywood on an existential edge, it is only fitting that this mask and gown from Maison Margiela Couture channeled a melting, possibly molten, Oscar. Ironically it was worn by Audrey Nuna, one of the performers from the Oscar-winning Best Song from KPop Demon Hunters, Golden.