Brad Pitt's Iconic Engagement Rings for Gwyneth, Jen and Angelina

Brad Pitt's Iconic Engagement Rings for Gwyneth, Jen and Angelina
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The Story Behind Brad Pitt's Iconic Engagement Rings

Brad Pitt may be one of Hollywood's most famous leading men, but he's also known for having an impeccable taste when it comes to engagement rings. Throughout his high-profile relationships with Gwyneth Paltrow, Jennifer Aniston, and Angelina Jolie, the rings Pitt used to pop the big question gave us major inspiration and highlighted key jewelry trends through the decades.

Gwyneth Paltrow's Pink Sapphire Stunner

When Brad Pitt proposed to Gwyneth Paltrow in 1996, their relationship was hugely popular. So it’s no surprise that her unique engagement ring also attracted tons of attention. The one-of-a-kind design features a large, oval-shaped pink sapphire flanked by two triangular diamonds set in 18k gold - a very on-trend style for the nineties.

The unusual pale pink gem was a very personal choice and seemed to perfectly capture Paltrow's colorful, carefree essence at the time. While their engagement only lasted a few months before they abruptly called it off, images of her statement jolie ring still linger as one iconic celebrity engagement memory.

Jennifer Aniston's Timeless Diamond Solitaire

After his split from Gwyneth, Brad moved on with actress Jennifer Aniston. While certainly more understated than Paltrow’s design, the ring Brad Pitt proposed with in 1999 established him as a purveyor of fine jolie rings. He selected an elegant oval-cut diamond set in a simple white gold solitaire band.

Channeling Hollywood glamour of decades past, this ring highlighted Aniston's easy, All-American beauty. It also kicked off a massive trend for oval diamond solitaires that continues today. Though they also divorced after a few years, Aniston's engagement ring remains an eternal style.

Angelina Jolie's Textured Table-Cut Stunner

In 2005, Brad Pitt began a famously turbulent relationship with actress Angelina Jolie. When they decided to marry, he once again customized a unique engagement ring to complement his future bride's personal style.

Featuring a massive 7-carat table-cut diamond, Jolie's ring has an organic, almost roughed-up quality. The raw uncut shape of the stone gives the ring an earthy, understated look compared to his previous polished and refined designs.

The platinum band is also engraved with unique decorations which give it an antique feel and add texture. Of all his engagements, this rough-hewn stunner seems to most closely align with the mysterious goddess vibes of Angelina Jolie herself.

What Makes Brad Pitt's Engagement Rings So Iconic

It's clear when you look at Brad Pitt's engagement history that he has an instinct for designing or picking out rings that are true showstoppers. But beyond having big diamonds and celebrity owners, what exactly makes them so iconic?

They Tell a Story

Each ring Brad chose reflects key traits of his distinctive fiancées. The pink sapphire complemented Gwyneth's youthful style. Jennifer's solitaire had a classic Hollywood beauty. And Angelina's organic shape captures her earthy spirit. Every detail told a story about who they were as a couple at that moment in time.

They've Stood the Test of Time

Even years and even decades after these boldfaced engagements took place, images of these rings continue to attract attention and influences jewelry styles. From dainty oval solitaires to rough-cut stones, Brad Pitt's timeless taste spawned many trends that remain popular for brides today. If that's not iconic, what is?

Everyone Has an Opinion

When you propose to an A-List actress with a jaw-dropping diamond, people take notice. The whole world weighed in with opinions on everything - from the settings, to the shapes, to the rumor mill firestorm around why certain relationships ended. It's hard to reach icon status without also garnering some controversy. #BRANGELINA forever!

Key Takeaways from Brad Pitt's Showstopping Engagement Rings

As a leading Hollywood heartthrob proposing not once but THREE times to famous actresses, all eyes were on Brad Pitt to deliver some swoon-worthy rings. And in the end, several clear lessons emerge from this engagement history:

Big diamonds will never go out of style. Even with his changing tastes, Brad consistently opted for diamonds with major carat weight because size does matter.

Custom details tell a personal story. Rings with unique shapes, engraved bands and colored gems seem to reflect the spirit of each fiancée.

Classics stand the test of time. Simple solitaires like Jen's will always comeback into vogue as new generations are inspired their elegance.

Whether he ended up staying with these ladies or not, Brad clearly has an impeccable taste when it comes to putting a ring on it. And the A-list worthy sparklers he proposed with continue to enchant us all.


What diamond shape did Brad Pitt pick for Gwyneth Paltrow?

Brad proposed to Gwyneth in 1996 with a unique pink sapphire oval flanked by triangular diamonds set in a gold band.

How big was Jennifer Aniston's engagement ring?

Jen's 1999 engagement ring featured an elegant 5-carat oval diamond solitaire set in a simple platinum band.

What details made Angelina Jolie's ring stand out?

Angie's 2005 engagement ring had a rough 7-carat uncut table diamond with an engraved platinum band for a textured look.

Why are Brad's rings considered so iconic?

The custom shapes reflected each woman's essence, spawned big jewelry trends, and still attract attention decades later.

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