Angelina Jolie vs. Jennifer Aniston: Whose Brad Pitt Engagement Ring Is Better?
- Photo: LACMA/Howard Pasamanick/Invision/AP1 of 22
- Photo: Michael Sanville/GettyImages.com2 of 22
- Photo: MARK J. TERRILL/Invision/AP3 of 22
- Photo: AP1/WENN4 of 22
- Photo: Kevin Mazur/WireImage5 of 22
- Photo: Fame Flynet6 of 22
- Photo: PATRICK GARDIN/Invision/AP7 of 22
- Photo: Nicolas Briquet/StarTraks8 of 22
- Photo: RWO/WENN9 of 22
- Photo: Eric Charbonneau/WireImage10 of 22
- Photo: Invision/AP11 of 22
- Photo: KM/Fame Flynet12 of 22
- Photo: Chris Pizzello/Invision/AP13 of 22
- Photo: WENN14 of 22
- Photo: Mr. Blue/WENN15 of 22
- Photo: LACMA/Howard Pasamanick/Invision/AP16 of 22
- Photo: LACMA/Howard Pasam/Promotional17 of 22
- Photo: DAN STEINBERG/Invision/AP18 of 22
- Photo: Fame Flynet19 of 22
- Photo: L. Cohen/WireImage20 of 22
- Photo: L. Cohen/WireImage21 of 22
Who wore it best: Brad's bling edition!
Before Brad Pitt popped the question to the mom of his six children, Angelina Jolie, he got down on one knee in front of Jennifer Aniston in 1999.
Both times, Pitt has collaborated with the jeweler designing his future fiancee's engagement ring. For Aniston's multi-level, swirl-design sparkler, he tapped Silvia Damiani; for Jolie's giant emerald-cut stone, he worked with their long-time jeweler and friend, Robert Procop.
But it looks like Pitt, 48, has gotten a bit more conservative when it comes down to the price tag. Back in 1999, Aniston's ring, which she debuted during a Sting concert in New York, was estimated to be worth around $500,000; jewelry expert Michael O'Connor quoted Jolie's ring to be somewhere around $250,000.
On Friday, Brangelina fans everywhere were rejoicing when Pitt's rep confirmed that the long-time loves were finally settling down and making things official. Jolie, 36, flashed her new engagement bling during a private art viewing at LACMA on Wednesday.
But lest we forget, before Aniston and Jolie, Gwyenth Paltrow stole Pitt's heart -- he proposed to her with a diamond sparkler in early 1997 after the pair dated for three years. They called off their plans to marry in June 1997.
MORE ON WONDERWALL:
The stars of "Orange Is the New Black" take Paris by storm on today's Celebs Gone Social.Watch Video »
Check out Kylie Jenner's most stylish swimsuit posts on today's Celebs Gone Social.Watch Video »
See how Sarah Michelle Gellar, Cindy Crawford and more stars celebrated Cinco de Mayo on today's Celebs Gone Social.Watch Video »
See what Hugh Hefner's former girlfriend has to say on Replay hosted by Wonderwall's Kirby Kristen.Watch Video »
Khloe Kardashian greets a giraffe, cuddles a chimpanzee and kisses a tiger cub on today's Celebs Gone Social.Watch Video »
Bares it All
"SYTYCD" star tWitch chats waxing for "Magic Mike XXL" and raps "The Fresh Prince of Bel-Air" theme song.Watch Video »