There’s something deeply satisfying about defying expectations, and Lily Li’s first major purchase was nothing if not defiant. Fresh out of university, she entered a Louis Vuitton boutique with her first paycheck from Arthur Andersen and left with a Stephen Sprouse collaboration bag that was more than an accessory—it was a manifesto.

“I still vividly remember taking out my credit card and purchasing the bag with extreme excitement but also a bit of imposter syndrome,” Li recalls of the now-vintage piece. Sprouse’s signature coloured graffiti, reflective of the artist’s pop-punk sensibility, stood out against the classic monogram canvas, as rebellious today as it was revolutionary then.

Growing up in post-Cultural Revolution China, Li was raised between worlds. Her mother, a poet and professor of Chinese literature, filled their home with Tang dynasty art, while her father ran an import-export business. “I was exposed to both Eastern and Western cultures—Beethoven and Tang dynasty poetry, coffee and tea, German cars and Chinese qipao,” she explains. It was this multifaceted upbringing that drew her to the luxury house’s collaboration that similarly bridged contrasting worlds.

The Louis Vuitton Stephen Sprouse partnership was considered radical when it was released in 2001. For Li, fresh from the competitive trenches of accounting, it was the perfect metaphor. “Graffiti represents street culture and rebellion, while Louis Vuitton stands for heritage and luxury. This collaboration celebrated self-expression by merging two seemingly opposite worlds,” says Li, now a senior investment counsellor with RBC Wealth Management. “I loved that bold statement.”

In a society where young women are often encouraged to be practical above all else, Li’s first splurge was a sign of independence. “It represented freedom,” she says simply. “It marked the first time I could buy something meaningful with money I earned myself. It was a powerful, liberating moment.”