Notable People
Can you guess which of Brad Pitt’s famous exes’ engagement ring is worth more now?
It’s been 10 years since Brad Pitt and Angelina Jolie announced their split. Of course, before Brangelina became a thing, Pitt was married to Jennifer Aniston. So just which superstar actress has the more expensive engagement ring?
Here are the details on Aniston and Jolie’s sparklers, and whose ring is worth more today.
Aniston’s engagement ring from Pitt
Pitt proposed to Jennifer Aniston in 1999, after the couple had been dating for about a year.
He worked with Italian jewelry designer Silvia Damiani on a custom “Eternity Swirl” ring. It featured a round 9-carat brilliant-cut diamond surrounded by multiple rows of smaller diamonds arranged in a spiral. The custom cascading spiral, set in platinum and white gold, was intended to symbolize eternity.
Several reports at the time estimated the ring’s value at about $500,000. So how much would it be worth now?
Mike Fried, CEO of The Diamond Pro, described the ring as “exceptionally unique” and estimated it has increased in value. “The ring was reported to cost $500,000 in 1999, meaning it would be worth approximately $1 million today.”
Pitt and Aniston married in July 2000 but separated in January 2005. Their divorce was finalized later that year. What happened to the Friends star’s engagement ring after their divorce has never been made public.
Jolie’s engagement ring from Pitt
Seven years after he and Aniston filed for divorce, Pitt asked Angelina Jolie to marry him.
For Jolie’s ring, Pitt worked closely with Beverly Hills jeweler Robert Procop to create a customized engagement ring and was heavily involved in the process for about a year.
As jewelry expert and Managing Director at Angelic Diamonds, Neil Dutta explained, “Robert already knew Angelina and her jewelry style incredibly well, too. The center diamond was actually cut to a shape and size specifically suited to Angelina’s hand, while the smaller diamonds were graduated in size and faceted to match. The result is a 6-carat elongated emerald-cut diamond at the center, with baguette-cut diamonds continuing around the platinum band.
“Overall, the ring totals an impressive 16 carats of natural diamonds. It was designed for Angelina down to the smallest details, rather than simply being an expensive diamond ring. The bespoke nature of the piece is an obvious factor. It’s a one-of-one design that took almost a year to create, with the diamonds cut specifically for Angelina’s hand. You’re not going to find another ring exactly like it.”
According to Dutta, Jolie’s ring could cost up to $1.35 million today, making it worth slightly more than Aniston’s.

