Usher's love affair with diamonds began early on. One could argue the "You Make Me Wanna..." artist's most iconic piece of jewelry is his glimmering "U" pendant necklace. As he dished in a 2023 video for GQ, he's upgraded his "U" necklace over the years, but the significance has never changed. 

In 2005, the music legend admitted to Forbes that he once splurged on a $100,000 customized bracelet that was studded with diamonds. Acknowledging that it was far from the most reasonable purchase he's ever made, Usher explained, "I know those things don't solidify success." That said, this hasn't stopped him from spending on more diamonds in the future. Years later, in 2022, the singer happily showed off his latest sparkly thing on Instagram: a diamond-encrusted toothpick. Once again, Usher commissioned jewelry designer Jacquie Aiche for his unique accessory.

Now, the singer might enjoy having various diamond-studded stuff, but he doesn't necessarily want diamonds on everything. This is especially the case when it comes to his expensive watches. As Usher said in the Daily Mail, "Occasionally it's cool to give your timepiece a little flash and wear something with diamonds in it, but I don't like it and I don't need it. I get more value in a watch's weight." That said, Damon Dash, the man behind luxury watch company Tiret and Usher's good friend, once gifted him a timepiece featuring over 1,000 diamond pieces. Needless to say, the singer didn't send that one back.