The sighting: Shark Tank reality TV personality Kevin O’Leary attended the 2026 Actor Awards in a sequined jacket and an accessory that elicited such a strong opinion in me that I’ve given it my lowest Judge the Jewels rating of all time.
The jewels: The piece in question is a custom Tiffany & Co. necklace.
It starts with an oversized, 100 carat diamond version of the maison’s HardWear chain and suspends a very unusual pendant: a bespoke diamond and ruby case that holds what is supposedly a very valuable sports trading card.
The “one of one” sports card is an autographed Michael Jordan-Kobe Bryant basketball card, a rare collector’s item that Page Six reports O’Leary purchased with three other people for $12.9 million this past August. O’Leary asserts the card is now worth $19.2 million.
O’Leary told AP reporters: “I’m looking at this card at the same way as if you could have bought a Picasso in 1962,” he added, noting that the historic investment piece has “done better than crypto.”
He is also wearing a bright red watch on each of his wrists: a one-of-a-kind Audemars Piguet and a Rolex Rainbow, both featuring rubies to match the pendant.
The trends: The main trend we see here – besides men in jewelry, watches on red carpets, and Tiffany hardwear – is shamelessly blatant displays of wealth.
What do we think? I try to approach this column with optimism and an open mind: when a celebrity’s jewelry doesn’t suit my personal style, I try to imagine who it would appeal to and see its allure through others’ eyes.
However…I can’t do that here.
This is painful to behold. It possesses no elegance or style. This man simply took the most portable, expensive thing he owns and hired Tiffany & Co to make a wearable display case so he could walk around and show it off.
It is a level of shameless self-aggrandizement that Jay Gatsby would find embarrassing.
When a celebrity wears expensive jewelry, it is still a display of wealth, yes, but it’s also an opportunity to showcase art, support talented artists, demonstrate taste, revel in the treasures of the Earth, and create moments of beauty.
This isn’t that. This is a 71-year-old man in sequins who has attached something expensive to his chest so that he can brag about the fact that he owns it.
A quick scroll of the comments on Instagram posts of the look revealed such astute reactions as “that’s what’s wrong with the world right here,” “I’ve never wanted to see someone get their chain snatched more,” and “I would disown my dad if he ever…”
Will this appeal to a certain subset of obscenely rich people with bad taste? Yes, probably, and you should feel free to accept those people’s money if they commission a similar design from you. Just don’t share the resulting monstrosity on your store’s social media or you’ll scare away your more discerning customers.
Judgement: -20 million/10 for the worst piece of red carpet jewelry I’ve ever seen.
Advertisement
