Jahleel Weaver’s pocket watch no longer keeps time. At least, not in the traditional sense. (With every wear, he’d have to reset it.)

For Mr. Weaver, though, the piece symbolizes something more meaningful: his decade-long career, from freelance styling assistant, to styling for Kylie Minogue in Australia, to deputy creative director of Fenty LVMH, to lead stylist and creative director of Rihanna and lead stylist of Dua Lipa.

The watch itself has evolved, too. What began as a vintage Rolex Datejust is now a custom Chrome Hearts wallet chain with a Rolex Datejust face attached. Mr. Weaver explained how a continued transformation has kept this piece of jewelry as aesthetically fresh as it is timeless. This interview has been edited and condensed for clarity.

Tell me about the one piece of jewelry that speaks to who you are.

It would definitely be a custom Chrome Hearts Rolex wallet chain that I had made with Chrome Hearts, maybe five or six years ago.

It started as the first expensive purchase I made when I got my first solo client as a freelance styling assistant. I bought myself a vintage Rolex Datejust. I’d been assisting for maybe two and a half, three years. And I was approached to work with Kylie Minogue, to style her for [multiple events and TV appearances that year]. This was early 2014. And I remember going to Australia, working with her, and I felt like, Wow, I’ve only been doing this for two and a half, three years, and I have a client. I wanted to do something special, because I felt very proud and very excited, and grateful for the opportunity. I bought it at a vintage jewelry store here in L.A. called Craig Evans Small. I wore that watch for years.

How did it go from watch to wallet chain?

I saw that Chrome Hearts would customize Rolexes. They basically just changed the band of my watch into a Chrome Hearts bracelet.