President John F. Kennedy proposed to Jacqueline Bouvier in 1953 with a distinctive toi et moi ring from Van Cleef & Arpels. The design featured a 2.88-carat diamond and a 2.84-carat emerald set side-by-side on a band accented with additional diamonds and emeralds.
While the details of the proposal are unclear, it's reported that JFK's father, Joseph Kennedy, selected the ring with help from a family friend at the jewelers. The engagement was announced in June 1953, though Jackie was not immediately photographed wearing a ring.
In 1962, after JFK took office, Jackie Kennedy had the ring redesigned. The reset version framed the original two stones with additional round and marquise-cut diamonds, a change meant to reflect her new public role as First Lady of the United States.
This unique ring is considered ahead of its time, sparking a trend for two-stone engagement designs that celebrities continue to embrace today.