Iconic Celebrity Engagement Ring Faceoff

2025 is officially here, and while January is a month famous for post-engagement celebrations (over 30 percent of the calendar year’s proposals take place in December!), it’s also the start of the NFL’s postseason. Over the next three weeks, teams from the American Football Conference (AFC) and the National Football Conference (NFC) will compete for a spot in Super Bowl LIX. However, here at BRIDES, we’re focused on a different kind of playoff picture. Rather than a competition based on touchdowns, field goals, and two-point conversions, we’re hosting a contest centered around carats, cuts, and gemstones. Welcome to the Ring Super Bowl!

Each week on our Instagram account, we’ll pit iconic engagement rings against one another in a diamond-shaped bracket and ask you to vote on your favorite; the winner of each match-up will advance to the next round of the competition. As for the engagement rings on our starting lineup? All of these sparklers are impressive in their own right. Some are known for their stunning cut or center stone, others are famous for their hefty price tag, and others still are simply iconic because of the couples they represent. And while some of these duos are no longer together, their rings (and relationships, for that matter) are remembered as important parts of pop culture.

We’ve stacked this roster to make choosing a winner challenging, but how you vote is entirely up to you: Perhaps you prefer one A-lister’s cushion-cut diamond, or find yourself more intrigued by a certain royal’s ring’s sapphire center. And while everyone has their own personal preferences when it comes to this all-important accessory, the question remains: Do others agree with your take? In our contest, you’ll be able to see and understand what the public actually thinks about some of the most well-known engagement rings as we narrow down our winner.

Before the competition can officially commence, we need to introduce you to our competitors. Spanning multiple decades, industries, and ages, the following engagement rings are some of the best we’ve ever seen—and now, we’re ready to put them to the test. Ahead, we break down the cuts, gemstones, price tags, and proposal stories behind each of these 16 rings, so you have a cheat sheet to reference each week.

Kate Middleton’s Heirloom Sapphire Engagement Ring

This is arguably one of the most famous engagement rings in the world. Prince William asked Kate Middleton to marry him with this 12-carat, oval-cut sapphire stone set in 18-karat white gold in 2010; the bauble famously once belonged to his mother, the late Princess Diana. The sparkler, which also includes 14 smaller diamonds, is reportedly worth close to $520,000. 

Meghan Markle’s Three-Stone Engagement Ring

Prince Harry proposed to Suits actress Meghan Markle in 2017 with a three-carat, cushion-cut diamond sourced from Botswana; Harry, who designed the ring on his own, had the diamond set on a gold band. While his late mother’s famous ring was already on the hand of the prince’s sister-in-law, Harry still found a way to honor her via his proposal piece: Two round diamonds from Princess Diana’s personal collection surround the center stone. The ring has only gotten sparklier over time, since the Duchess of Sussex upgraded the ring’s gold band to pavé shortly after her son’s birth in 2019.

Jennifer Lopez’s Pink Diamond Engagement Ring

When Ben Affleck proposed to the Jennifer Lopez for the first time in 2002, he did so with a six-carat, radiant-cut pink Harry Winston diamond. The ring, which also included two white diamonds on either side of the center stone, reportedly cost $2.5 million. The A-list duo ultimately postponed—and later called off—their nuptials just one day before they planned to tie the knot in 2004. 

Jennifer Lopez’s Green Diamond Engagement Ring

For Lopez and Affleck, everything was bigger—and a bit more expensive—the second time around. When the couple reconnected in 2021, it wasn’t long before the Deep Water actor re-popped the question to the “Jenny from the Block” singer. In 2022, the Maid in Manhattan star stepped out wearing a $5.6 million-dollar green diamond set on a platinum band and surrounded by two half-moon-shaped diamonds. While the sparkler included a message of the actor’s commitment to the singer (“not.going.anywhere.”), Lopez ultimately filed for divorce on August 20, 2024, exactly two years after they tied the knot. 

Hailey Bieber’s Oval-Cut Diamond Engagement Ring

In 2018, Hailey Baldwin became “one less lonely girl” when Justin Bieber asked her to marry him with a solitaire, oval-cut diamond set on an 18-karat gold band that’s reportedly worth $500,000. The singer proposed while the two were vacationing in the Bahamas and subsequently announced the news with a lengthy Instagram post. 

Sofia Richie’s Emerald-Cut Diamond Engagement Ring

Sofia Richie, a social media star and model, said “yes” to marrying Elliot Grainge, a British record executive, in April 2022. Grainge, who had known Richie for years before they started dating in 2021, proposed with a six-carat emerald-cut diamond in a platinum solitaire setting designed by Stephanie Gottlieb. The proposal, which took place in Hawaii, featured an ethereal aisle lined with pillar candles and scattered with petals leading to a table outfitted with a bottle of chilled Champagne. 

Serena Williams’ Oval-Cut Diamond Engagement Ring

After first meeting at the Cavalieri Hotel in Rome before she was scheduled to play in the 2015 Italian Open, Reddit founder Alexis Ohanian returned to the same spot to propose to tennis star Serena Williams. Ohanian got down on one knee with a ring featuring an oval-cut center stone surrounded by two smaller diamonds on a platinum band; the piece has an estimated worth of approximately $2 million. 

Ciara’s Brilliant-Cut Diamond Engagement Ring

When it came time for Pittsburgh Steelers quarterback Russell Wilson to propose to the pop star in 2016, he did so with a 16-carat, brilliant-cut diamond surrounded by trapezoid and pear-shaped diamonds that clocked in around $2.5 million. Wilson quickly took to Instagram after Ciara said “yes,” sharing a video of the two celebrating on a beach in the Seychelles. 

Olivia Culpo’s Three-Stone Oval Diamond Engagement Ring

Four years after Olivia Culpo and Christian McCaffrey started their relationship, the running back for the San Francisco 49ers got down on one knee on April 2, 2023, and asked the former Miss Universe to marry him. He did so with a three-stone oval diamond ring surrounded by epaulette side stones and set in a handcrafted gold and platinum setting. The piece, which McCaffrey worked with Ring Concierge to design, is worth between $100,000 to $200,000. 

Angelina Jolie’s Art Deco-Inspired Engagement Ring

The actors, who first met on the set of Mr. and Mrs. Smith, got engaged when Brad Pitt presented Angelina Jolie with a 16-carat, emerald-cut diamond surrounded by trapezoid baguette stones. The Art Deco-inspired ring, which Pitt was reportedly heavily involved in the design of, was created by Robert Procop and is reportedly valued at $250,000. 

Jennifer Aniston’s Cushion-Cut Solitaire Diamond Engagement Ring

In 2012, Justin Theroux asked Jennifer Aniston to marry him nearly seven years after her high-profile split from Pitt. He did so with a a nine-carat, cushion-cut solitaire diamond ring worth approximately $1 million—$500,000 more than her nine-carat, brilliant-cut stone from her famous first husband. While the two eventually filed for divorce in 2018, they still remain close friends. 

Lily Collins’ Rose-Cut Morganite Engagement Ring

Opting for something out of the ordinary, Charlie McDowell, a film director and screenwriter, proposed to Lily Collins, the star of Emily in Paris, with a rare rose-cut morganite ring designed by jeweler Irene Neuwirth; the moment unfolded during a hike, per the actress’ engagement announcement post on Instagram in 2020. With an estimated weight between two and three carats and price tag of around $4,000, the stone was set in a diamond halo with a brushed gold setting. Unfortunately, in May 2023, the sparkler was reported stolen from a spa locker room, along with the actress’ wedding band. The ring pictured here is Collin’s replacement bauble, which is nearly identical to the original; the duo appears to have made a few modifications during the redesign process, opting for the same bezel setting, but mixing metals (gold and platinum) to maximize shine.  

Selena Gomez’s Marquise-Cut Engagement Ring

Songwriter Benny Blanco popped the question to actress and singer Selena Gomez in late 2024—and quickly sent the internet ablaze over the marquise-cut engagement ring he chose for her (and a viral theory that he proposed while they were shooting a Taco Bell commercial!). While confirmed details about the sparkler, which was designed by Katherine Theofilos Claster and Stephanie Theofilos of Abril Barret, have yet to emerge, People reports that it’s thought to be a six-carat diamond worth $225,000. 

Samira Wiley’s Princess-Cut Solitaire Diamond Engagement Ring

This duo has Orange Is the New Black to thank for their coupling. After meeting on the set of the hit Netflix show, Lauren Morelli decided to propose to Samira Wiley in October 2016 while the two were on vacation in Palm Springs; she did so with a princess-cut solitaire diamond on a gold band. They returned to the locale in March of the following year to tie the knot. 

Katy Perry’s Flower-Shaped Ruby Engagement Ring

In the ultimate romantic gesture, Pirates of the Caribbean actor Orlando Bloom proposed to “Firework” singer Katy Perry on Valentine’s Day in 2019 while the two were on a helicopter ride. The stone’s color even matched the holiday, as Bloom selected a flower-shaped ring featuring a ruby center stone encircled in smaller diamonds.

Gisele Bündchen’s Cushion-Cut Diamond Engagement Ring

A football star and a supermodel walk into a bar—and immediately fall in love. That’s the story for Tom Brady and Gisele Bündchen who first crossed paths at a wine bar in New York City in 2006. The quarterback proposed just two years after that initial meeting with a four-carat, cushion-cut diamond estimated to be worth just shy of $150,000. However, after being married for 13 years (and having two children together), the couple called it quits in 2022.