The 2026 awards season may finally be wrapped, but the fashion chaos it delivered still lives rent-free in everyone’s heads.
From jaw-dropping couture to looks that had the internet collectively asking, “Is this legal,” this year’s red carpets blurred the line between bold and downright unhinged fashion moments.
From stars like Chappell Roan, whose Grammys appearance instantly went viral thanks to a controversial breast-piercing dress, to Emilie Livingston’s Oscars look that left her backside completely exposed, these outfits didn’t just miss the mark; they became cautionary tales of what a fashion “fail” can be.
Now that the dust has settled, here are 22 of the biggest fashion missteps and most chaotic outfits that made this awards season unforgettable, for better or worse.
#21 Kim Kardashian
Kim Kardashian attended the 2026 Oscars afterparty in a custom, form-fitting, glittering gold gown by Gucci, fresh off the Milan Fashion Week runway.
The dramatic long-sleeved dress was designed by Demna and hugged her silhouette with shimmering fabric that caught the light as she posed for photos.
Many labeled her look a “mess,” with several critics specifically targeting the hairstyle she chose for the appearance.
One critic wrote, “All that dress and makeup just for your hair to ruin everything,” while another added, “She is definitely regretting her hairstyle choice today lol.”
A third commenter wrote, “Body is still serving—that gold sequin gown is hugging every curve like it owes her money. But sis… the hair/voluminous wig situation is fighting for top billing. Who approved that? Dress 10/10, hair needs a timeout.”
One netizen said, “I love it when they can’t walk in their million-dollar gown.”
Others questioned, “Why was [Kim] even there to begin with?”
The dramatic long-sleeved dress was designed by Demna and hugged her silhouette with shimmering fabric that caught the light as she posed for photos.
Many labeled her look a “mess,” with several critics specifically targeting the hairstyle she chose for the appearance.
One critic wrote, “All that dress and makeup just for your hair to ruin everything,” while another added, “She is definitely regretting her hairstyle choice today lol.”
A third commenter wrote, “Body is still serving—that gold sequin gown is hugging every curve like it owes her money. But sis… the hair/voluminous wig situation is fighting for top billing. Who approved that? Dress 10/10, hair needs a timeout.”
One netizen said, “I love it when they can’t walk in their million-dollar gown.”
Others questioned, “Why was [Kim] even there to begin with?”
4points
#22 Kylie Jenner And Timothée Chalamet
Timothée Chalamet and Kylie Jenner made a joint appearance at the star-studded 2026 Oscars afterparty despite Chalamet’s loss in the Best Actor category earlier that evening.
The pair opted for contrasting monochrome looks for the event, as Jenner wore a custom black sequin gown by Alexander McQueen featuring a plunging halter neckline, a hip cutout, and a feathered train.
Chalamet, meanwhile, opted for an all-white leather suit by Chrome Hearts paired with matching high-top sneakers.
One disappointed user harshly critiqued their outfits, writing, “Both looking a mess, no shade.”
“Timothee took whatever he saw in the closet and wore it,” commented another.
“Both looking a mess. They need a stylist. Bad,” another critic added.
The pair opted for contrasting monochrome looks for the event, as Jenner wore a custom black sequin gown by Alexander McQueen featuring a plunging halter neckline, a hip cutout, and a feathered train.
Chalamet, meanwhile, opted for an all-white leather suit by Chrome Hearts paired with matching high-top sneakers.
One disappointed user harshly critiqued their outfits, writing, “Both looking a mess, no shade.”
“Timothee took whatever he saw in the closet and wore it,” commented another.
“Both looking a mess. They need a stylist. Bad,” another critic added.
1point
