From gowns that leave little to the imagination and ill-fitting tuxedos, the 2026 Academy Award red carpet was filled with fashion don’ts.
The end of awards season has kicked off as stars begin arriving at the Dolby Theater in Los Angeles Sunday night to watch Conan O’Brien host the award show for the second year in a row.
And while some celebrities are wowing with their looks, capturing the essence of old Hollywood with understated couture, satin galore, and crystal-encrusted designs, others are completely missing the mark, wearing outfits that are either too revealing, not tailored properly, or ill-suited for the lavish occasion the event calls for.
For instance, Canadian TV personality Kevin O’Leary chose to accessorize with 2004-vintage NBA cards with no explanation, while Amelia Dimoldenberg — the host of the popular YouTube series “Chicken Shop Date” — played it safe with an unimaginative black gown that didn’t stand out from the crowd.
Here are some of the most questionable looks from the 2026 Oscars:
Jayme Lawson
While the ‘Sinners’ actor suited the dark purple color of her gown, the middle section of the silhouette was not flattering, drawing comparisons to a candlestick holder (Getty Images)
The fringe sequinned dress completed the look with a slick-back updo (Jordan Strauss/Invision/AP)
Kevin O’Leary
The Canadian businessman dressed way too flashy as he stood out with his black tuxedo adorned with medieval characters (Getty Images)
O’Leary also chose the Oscars to show off his 2004 NBA cards that are supposedly worth $20 million, which confused red carpet viewers (AFP via Getty Images)
The diamond-encrusted card is of the late Kobe Bryant (AFP via Getty Images)
Amelia Dimoldenberg
The host of the iconic ‘Chicken Shop Date’ series wore a vintage Ralph Lauren Collection gown with a large strip of fabric in the back that hindered the gown’s overall silhouette (Getty Images)
Dimoldenberg accessorized with a boring updo and a plain silver necklace (Getty Images)
