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The pair not only posed for photos at the event in the South of France, but they took some time to catch up poolside at Leo's luxurious French estate.
The star-studded event was also graced by Heidi Klum, Sean Penn, Lenny Kravitz, who performed for guests, and even Titanic co-star Billy Zane - who took to Instagram to share their reunion with fans, twenty years after the film's release.
Cosying up together at the bash, the actor, 51, playfully joked in the caption: 'Gangs all here. Go figure...'Still looking good: Adding a gold necklace of his own, the star kept casual as he spent a day relaxing with Kate - with his hair swept naturally to the side, proving him to be as handsome as his younger Titanic days (R) two decades later Close: The pair later attended Leo's foundation charity gala that night (above) - with Leo in a slick suit and Kate in a slinky black dress - where they auctioned off an intimate dinner with them in NYC as the top fundraising prize Kate and Leo both rocketed to super-stardom after playing star-crossed lovers Rose De Witt Bukater and Jack Dawson in the 1997 classic Titanic - and have remained close ever since.
Closer than ever: Clearly with quite a bit to catch up on, the two friends were seen chatting on the deck of Leo's villa as they soaked up the sun, before they walked back into the house with their arms wrapped affectionately around each other Leonardo Di Caprio and Kate Winslet were reunited in Saint Tropez recently and it was almost as if no time had passed at all since they starred in Titanic together.
Leo looked as dapper as ever in his Vilebrequin swim shorts, but it was Kate's scalloped bikini that really caught our attention!
Keeping casual ahead of their glamorous evening, the mum-of-three added a selection of delicate gold necklaces and tied her look together with oversized dark sunglasses.