Who wore it best: Brad's bling edition!
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.