Was Jackie Kennedy or Carolyn Bessette-Kennedy’s Engagement Ring More Expensive? Comparing Their Stunning Sparklers

26-Feb-2026: Two of the most iconic women in American history — Jacqueline Kennedy Onassis and Carolyn Bessette-Kennedy — wore engagement rings that perfectly reflected their eras and personal styles.

But when it comes to price and value, which Kennedy engagement ring was more expensive?

Let’s compare their stunning sparklers.

Jackie Kennedy’s Engagement Ring

When John F. Kennedy proposed to Jackie in 1953, he presented her with a breathtaking ring from Van Cleef & Arpels.

Ring Details:

• Design: Toi et Moi (two-stone setting)
• Stones: 2.88-carat diamond + 2.84-carat emerald
• Upgrade: Later surrounded by marquise-cut diamonds in 1963

The emerald-and-diamond combination was rare for the time, giving the ring a European, aristocratic feel.

Estimated Value Today:

Experts estimate Jackie Kennedy’s engagement ring would be worth $500,000 to over $1 million today, factoring in:

• Premium gemstones
• Designer prestige
• Historical significance

The provenance alone dramatically increases its market value.

Carolyn Bessette-Kennedy’s Engagement Ring

When John F. Kennedy Jr. proposed to Carolyn in the mid-1990s, her ring reflected her minimalist fashion aesthetic.

Ring Details:

Style: Classic diamond solitaire

Cut: Emerald-cut diamond

Carat Size: Estimated 4–5 carats

Setting: Platinum band

Her ring became a symbol of ’90s quiet luxury and remains a top inspiration for modern brides.

Estimated Value Today:

A high-quality 4–5 carat emerald-cut diamond can range between $200,000 and $600,000, depending on clarity and color.

Which Kennedy Engagement Ring Was More Expensive?

Based on current estimates:

Jackie Kennedy’s engagement ring was likely more expensive.

Reasons include:

• Two significant center stones
• Additional diamond enhancements
• High-end designer craftsmanship
• Presidential and historical provenance

While Carolyn’s ring featured a larger single diamond, Jackie’s combination of rare gemstones and historical importance gives her ring the higher estimated value.

How many carats was Jackie Kennedy’s engagement ring?

It featured a 2.88-carat diamond and a 2.84-carat emerald.

What cut was Carolyn Bessette-Kennedy’s ring?

Her ring is widely believed to feature an emerald-cut diamond.

Why is Jackie Kennedy’s ring more valuable?

It includes two premium gemstones, designer prestige, historical significance, and later diamond enhancements.

Is either ring available for purchase today?

Jackie Kennedy’s ring was auctioned in 1996 and is now privately owned. Carolyn’s ring remains in private hands.