Miley Cyrus, the three-time Grammy winner, got people to thinking recently when she posted a tale about her first major purchase. This item has lived in a special place in her heart in recent years. Even years later, Cyrus can perfectly describe her first angel investment. She bought it—notably, at auction, not in person—while she was still starting out her career as a young actress. This dress, which was expected to sell for up to $8,000, is one of the jewels of her collection.
Miley Cyrus, in comparison, became an international superstar at the age of 13. She gained immense popularity as the titular character in Disney Channel’s “Hannah Montana.” The show began airing in 2006 and continued through 2011. It propelled her into the public spotlight and allowed her to amass her fortune from a young age. In the years that ensued, Cyrus fell in love with style, frequently spending the money she made on acting to buy one-of-a-kind items.
Now 32, Cyrus looks back on the biggest purchases of her life with a mix of nostalgia and incredulity. A black perforated Alaia belt is one of them, and she still has it. “But I do in fact have it,” she proclaimed in an interview last month with The New York Times. Today, perforated Alaia belts go for $850-$1,750. Perhaps this indicates that early on in her career, Cyrus curated her wardrobe wisely with a goal in mind.
On May 5, 2025, Cyrus showcased her penchant for fashion once again at the Met Gala, where she wore a custom crop top and skirt designed by Bob Mackie. The move might seem ostentatious, but the event exemplified her tight relationship with the designer. She has found inspiration in his work since the early days of her career.
Cyrus is not the only one looking back fondly on their first purchase. Similarly, celebrity Kevin Hart talked about the impact of his first major purchase. He purchased throwback jerseys from a handful of favourite athletes! Reflecting on his own choices, Hart humorously remarked, “If I had to put a number on it, I would say it was stupid plus stupid, which equals stupid, OK? I don’t even feel comfortable talking about it.”
Clothing, for one, has become a favored category for instant millionaires’ first big celebrity purchases. Cyrus’s early acquisition of the Bob Mackie dress exemplifies this trend as many young stars often invest in fashion items that resonate with their personal style and aspirations.
For one, it’s very obvious that Cyrus idolizes designer Bob Mackie, which has heavily impacted her style. While the actual cost of her Bob Mackie gown remains a mystery, her love of his craft sure had us all dreaming. Her emotional attachment to her purchases exposes the profound meaning behind these objects. They mean so much more to her than their monetary value.
It is through their originality that artists such as Cyrus have inspired a generation of creators. The singer’s journey from child star to a recognized force in the music industry illustrates how formative experiences contribute to one’s identity and tastes.