When Eugenio Pirri was growing up in British Columbia, his family would often give keepsake gifts to him and his two older sisters to mark memorable occasions. He still cherishes many of them, including a razor with a stainless steel handle engraved with the date June 1984, the month he started shaving.

As an adult, his appreciation of meaningful mementos hasn’t waned. In 2002, Mr. Pirri bought himself a present: a 31-millimeter quartz stainless steel Cartier Tank Française.

“I got a big bonus and I thought, ‘I’m going to treat myself to a luxury item,’” said Mr. Pirri, now one of the two chief executives of Dorchester Collection, a group of hotels and residences. He was sitting in his office in the Knightsbridge neighborhood of London, not far from the flagship hotel that bears the brand’s name. On one wrist was that watch; on the other, he wore a Cartier Juste Un Clou bracelet, part of a daily rotation from a personal jewelry collection that includes pieces from Tiffany & Company, Bulgari, and Hermès.

When he purchased the watch, Mr. Pirri, now 53, was working as the human resources manager at the W San Francisco hotel. He liked timepieces and had several, including a gold Longines that his parents gave him for his high school graduation. But, when it came to buying a keepsake piece for himself, he said, “I didn’t really look at watches, just because I couldn’t afford watches.”

By that point, however, he had developed a love of designer clothing and accessories: He had a Prada bag, and owned loafers and a belt by Gucci. It was his personal passion, although his mother, who worked in the delicatessen his parents owned, had a collection of ruby jewelry.