How Does Angelina Jolie’s Engagement Ring Compare to the One Brad Pitt Gave Jennifer Aniston?

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Jolie in March, with detail of her new ring inset (Jason Kempin/Getty Images, LACMA, inset)

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Aniston in February, with her ring inset (Jason Merritt/Getty Images, Kevin Winter/Getty Images, inset)


Since Angelina Jolie and Brad Pitt's engagement was announced last week, there has been so much buzz about the ring, the ring, the ring, which designer Robert Procop and Pitt collaborated on for over a year in order to get it just right. But long before we had ever heard of Brangelina, Pitt famously popped the question to his first wife, Jennifer Aniston, making us wonder how the two rings — both of which he helped create — stack up.

[Related: It's Official — Brad Pitt and Angelina Jolie Are Engaged]

As we saw on Friday, Jolie's ring features a massive giant emerald-cut stone, set in platinum, with side stones that encircle her finger. There are varying reports of the price of the bauble — ranging from $250,000 to $1 million — but it's hard to determine the cost without knowing the carat count, which the couple didn't share when they made their engagement announcement. What we do know, courtesy of jeweler Procop is that, "Each diamond is of the highest gem quality." And jewelry expert Michael O'Connor — who estimates that it's a 6-carat ring with about $250,000 — told Us Weekly, "Emerald cut diamonds have fewer facets so they don't have the sparkle of other cuts, but that also means that they need to be the best quality. The light returned from a diamond like this is pure and white."

[Related: Brad Pitt and Angelina Jolie In Talks to Co-Star in New Movie]

When Pitt asked Aniston to marry him back in 1999, Silvia Damiani designed a special sparkler — which appears to be smaller than Jolie's — for the actor's then-girlfriend. "The story began when casually, Brad Pitt had liked a pair of earrings I had designed after these had won the Diamond International Awards," Damiani told Business Today. "He then requested a special item for his engagement to Jennifer Aniston based on this same model." The custom design, which was a symbol of eternity, featured a round stone surrounded by three rows of 20 spiraling diamonds. At the time it was valued at around $500,000. The designer later created Pitt and Aniston's wedding bands, which were made of white gold, diamonds, and engraved. Aniston's said "Brad 2000," while Pitt's said "Jen 2000."

Both rings are stunners, but they're certainly different. Aniston's has a classic feel to it — Pitt reportedly wanted it to look like a heart to symbolize their everlasting love — and the rows of diamonds give it a can't-miss sparkle. On the other hand, Jolie's has a look that's more in line with modern architecture enthusiast Pitt's style. It has a large, perfectly cut diamond centerpiece with stones that gradually decrease in size around it — almost in a crown-like shape. And, as O'Conner noted, the cut of the gem mutes the brilliance of the diamonds, so it doesn't have the same attention-grabbing shimmer that Aniston's does.

Of course, we can't forget that Pitt was also previously engaged to Gwyneth Paltrow, whom he dated from 1994 to 1997, so he's had quite a bit of experience when it comes to engagements rings.

Which ring do you like more: Jolie's or Aniston's? Weigh in.

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