1. Metallic Jewel Sandal, 2. Jamila Thong Sandal, 3. Kirna Zabête at Nine West Sunfish Gold Sandal, 4. Musa London Sandal, 5. Embellished Thong Sandal F. Martin Ramin/The Wall Street Journal, Styling by Anne Cardenas

ACCORDING TO Costanzo Canfora, the general manager of Canfora Capri, the first jeweled sandal was made by his grandfather Amedeo Canfora, in the early 1950s. "Everyone went crazy," said Mr. Canfora, 36, who carries on the business that his grandfather established on the Italian island in 1946. "Before, no one had thought to make sandals with jewels."

As he tells it, few women of his grandfather's era, including Jacqueline Kennedy—who, he said, first came to Canfora in 1962—left the island without a visit to the family shop. Jeweled sandals "are perfect for nighttime in Capri," said Mr. Canfora. "It's not so easy to walk here in high heels. Flat sandals are the most comfortable shoes to go around the island."

Six decades later, jeweled sandals are still ideal for steamy summer nights (or days), whether you're navigating the craggy streets of Capri or a smooth city block. They often still evoke Jackie dashing around in her white jeans, head scarf and oversize sunglasses. It's an association that makes the sandals decidedly un-edgy—which is OK. When it's so hot outside, it's better not to strain so hard to seem cool.

—Meenal Mistry

1. Metallic Jewel Sandal, $775, Giuseppe Zanotti Design, 212-650-0455

2. Jamila Thong Sandal, $300, canfora.com

3. Kirna Zabête at Nine West Sunfish Gold Sandal, $79, ninewest.com

4. Musa London Sandal, $495, net-a-porter.com

5. Embellished Thong Sandal, $78, Victoria's Secret Catalogue, 800-888-8200