The 49-year-old singer and actress - who received the prestigious Michael Jackson Video Vanguard Award and performed a medley of her hits at the ceremony on Monday (20.08.18) - was decked out from head to toe in glittering Tiffany & Co diamonds that cost over $2 million (about R29million).
Jennifer's stylist Rob Zangardi told Vogue Australia: "Her look is always a little bit couture, a little bit street - she might wear a couture gown with big hoops and tons of gold necklaces.
"Naturally, the earrings Jennifer chose for the VMA awards were the most expensive ones on the tray. She knows her jewels!"
Rob and his partner, Mariel Haenn, spent nearly two months working on Jennifer's VMAs looks, with the singer opting for custom Versace to perform 'Love Don't Cost a Thing', 'All I Have' and 'Jenny From the Block'.
Rob added: "I was actually with Jennifer when she found out she was getting the Video Vanguard Award, and it was sort of a full-circle moment for me and Mariel, as well as for Jen.
"We met at MTV, and 20 years later, we're standing next to Jennifer before she accepts an award. It was a really epic night."
Rob and Mariel have worked with Jennifer for eight years, handling the costumes for all of her performances since then, including her Las Vegas residency.
Rob said: "The way we break down all of her show costumes is by sections-there's always a Latin section, a hip-hop section, and for the VMAs, it was all about her greatest hits, so we knew there would be a full variety,"
"We knew we had to make the biggest impact in the shortest amount of time, so we were adding layers, taking off layers, using tearaways. . . . And the first brand we thought of was Versace, because she's had such a long relationship with them. They know how hard she dances, and that she's going to be suspended from the ceiling and needs the mesh, the snaps, the stretch fabric so she can move."