The Most Iconic Celebrity Engagement Rings (and What They Started)

The most iconic celebrity engagement rings are not necessarily the most expensive ones — they are the ones that changed what everyone else asked for. Princess Diana's oval sapphire, Jackie Kennedy's two-stone toi et moi, Audrey Hepburn's stack of slim bands, Jennifer Lopez's pink diamond, Hailey Bieber's elongated oval and Zendaya's sideways cushion each walked out of one famous proposal and straight into a thousand jewellers' order books. This is the story of those rings — not what they cost, but what they started. (If it is eye-watering price tags you are after, we have covered the world's most expensive engagement rings separately.)

Jackie and Audrey: the mid-century rule-breakers

Two of the most influential rings of the twentieth century arrived within a year of each other, and neither looked anything like the solitaires of their day.

In 1953, John F. Kennedy proposed to Jacqueline Bouvier with a Van Cleef & Arpels toi et moi — French for "you and me" — that set a 2.84-carat emerald and a 2.88-carat diamond shoulder to shoulder, flanked by tapered baguettes. By most accounts it was Joseph Kennedy, the ambitious father-in-law, who actually chose it. Jackie sent the ring back to Van Cleef & Arpels in 1962 to be reset with additional round and marquise diamonds, which tells you something true about her: she treated even an heirloom as a living piece of style. Seventy years on, the toi et moi is one of the most requested settings in the world — Ariana Grande and Megan Fox both wore modern versions — and every one of them traces back to that 1953 original.

A year later, in 1954, Mel Ferrer gave Audrey Hepburn something quieter and, for its time, stranger: not one ring but a trio of slim bands — by most accounts a baguette-diamond eternity band in white gold with plain companions in rose and yellow gold — meant to be worn together or separately depending on her outfit. In an era when a solitaire flanked by baguettes was practically compulsory, a mix-and-match set was almost eccentric. Today "ring stacking" is one of the biggest movements in bridal jewellery, and Audrey got there roughly seven decades early.

Princess Diana's sapphire: the most copied ring on Earth

No engagement ring in history has been imitated more than the one Lady Diana Spencer chose in 1981: a 12-carat oval Ceylon sapphire encircled by fourteen diamonds, set in 18-carat white gold by Garrard, then the Crown Jeweller. The famous scandal of it — and the secret of its influence — is that it was not a bespoke royal commission. Diana picked it from Garrard's existing collection, reportedly priced around £28,000, meaning anyone with the money could order the same ring. Some in royal circles are said to have sniffed at that. The public understood it instantly: the future Princess of Wales wore a ring you could actually buy.

The effect was immediate and has never really stopped. Sapphire-and-halo rings surged through the 1980s, and when Prince William proposed to Kate Middleton with his mother's ring in 2010, the whole cycle repeated for a new generation. It remains the single most influential coloured-stone engagement ring ever made — proof, decades before anyone said it out loud, that an engagement ring does not have to be a white diamond at all. If you are curious how the diamond solitaire became the "default" that Diana broke from in the first place, our history of diamond engagement rings traces that story.

Jennifer Lopez and the colour craze — twice

Few people have started an engagement-ring trend twice, twenty years apart, with the same man. In 2002, Ben Affleck proposed to Jennifer Lopez with a 6.1-carat radiant-cut pink diamond from Harry Winston, reportedly worth around $2.5 million. Natural pink diamonds are among the rarest gems on Earth, and before that proposal almost nobody asked for one. Afterwards, pink became the celebrity stone: Mariah Carey's 2008 ring carried 17 carats of pink and white diamonds, Blake Lively received a light-pink oval in 2012, and searches for pink diamonds climbed across the industry.

The first engagement famously ended, but when the couple reunited, Affleck proposed again in 2022 — this time with an 8.5-carat natural green diamond flanked by white side stones and engraved inside with "not.going.anywhere." Natural green diamonds are rarer still than pinks — only a few hundred above a carat are thought to exist — and the ring set jewellers talking about green as the next colour frontier. Two proposals, two of the rarest stones in existence, two waves of couples asking their jeweller, "Can I have something in colour?"

Meghan Markle's trilogy: meaning over size

When Prince Harry proposed to Meghan Markle in 2017, the ring he designed with Cleave & Company was, by royal standards, restrained: a cushion-cut centre diamond of roughly three carats sourced from Botswana — where the couple had holidayed early in their relationship — flanked by two smaller round diamonds from Princess Diana's personal collection, all on a slim yellow-gold band. Harry reportedly wanted the centre stone to be traceably, ethically sourced.

What it started was less a look than a way of thinking. The three-stone "trilogy" setting — past, present and future — boomed after 2017, and so did something deeper: couples began asking where their stone came from, and whether a ring could carry a story rather than just a carat weight. That instinct, more than any celebrity, is part of why traceable lab-grown diamonds have grown so quickly since; we have written about the ethics and sustainability of lab-grown diamonds in that light.

Hailey's oval and Zendaya's east-west: the modern shape-shifters

The most powerful trendsetter of the social-media era is arguably Hailey Bieber. When Justin Bieber proposed in the Bahamas in July 2018 with an elongated oval solitaire by New York diamond house Solow & Co. — reportedly somewhere between six and ten carats, on a plain gold band — the round brilliant's long dominance finally cracked. Ovals look larger than rounds of the same carat weight and flatter the finger, and once photographs of Hailey's ring circulated, jewellers everywhere heard the same request: an oval, please, and make it long. The oval boom is still running eight years later, stretching into ever-more-elongated proportions.

Then, at the 2025 Golden Globes, Zendaya quietly rewrote the brief again. Her ring from Tom Holland — a 5.02-carat elongated cushion by London designer Jessica McCormack, held in a Georgian-inspired button-back setting on a gold band — turned the stone sideways, running east-west across the finger rather than north-south. East-west settings existed before, usually for emerald or marquise cuts, but almost never for cushions; within months, jewellers were reporting a wave of east-west requests. It is a useful reminder that the same diamond can feel entirely different depending on how it sits on the hand.

At a glance: eight rings, eight trends

Notice what none of these rings started: a race to the biggest stone. Diana's ring was famously off the shelf; Meghan's centre diamond was modest by royal standards; Audrey's bands held barely a carat and a half of diamonds between them. What made each one iconic was a choice that felt exactly like its wearer — a colour, an orientation, a story — made confidently before anyone else was doing it.

That, honestly, is the only lesson we would take from any of them. At Signora, every ring is made to order in our Surat workshop around a lab-grown diamond that is IGI certified, with the report number laser-inscribed on the girdle — so whether your version of iconic is a Hailey-style elongated oval or a Zendaya-style east-west setting, the stone's story is verifiable rather than mythical. If you are starting your own search, our engagement ring guide is a calm place to begin, and our engagement ring collection shows what these ideas look like when they are yours.