Strolling through Times Square back in ’98 wasn’t just about catching a glimpse of a billboard; it was an experience. Long before the days of “influencers” and perfectly crafted Instagram posts, there was this raw, cinematic vibe buzzing at the intersection of 5th and Broadway. At the center of this vibe were Mark Vanderloo and Esther Cañadas—the quintessential creators of “New York Cool.”

The Essence of “Urban Minimalism” The late ’90s ushered in a major transformation in fashion. We were stepping away from the bold, structured styles of the ’80s and embracing a more subdued, sleek aesthetic. This was the time of Urban Minimalism, where it wasn’t about going overboard, but rather nailing the basics—a flawless white tee, a tailored charcoal blazer, and a leather trench that seemed straight out of a film noir.

Mark and Esther weren’t just wearing these outfits; they truly embraced them. From their iconic DKNY ads captured by Peter Lindbergh to their “off-duty” moments at the VH1 Fashion Awards, they exuded a refined simplicity that feels strikingly relevant in 2026.

The DKNY Effect: Romance on a Billboard Their relationship was the fashion world’s worst-kept (yet most adored) secret. After crossing paths on a DKNY shoot in 1997, they became the brand’s go-to muses. The Aesthetic: Grainy black-and-white snaps, yellow cabs, and that effortlessly tousled hair. The Vibe: They appeared as two stunning strangers sharing a fleeting moment amidst the hustle of Manhattan. Their wedding in 1999 was the pinnacle of this era—a high-fashion “I do” where they donned Donna Karan, cementing their reign as the decade’s ultimate power couple. 

We’re all yearning for that “less is more” mindset. Mark Vanderloo, who you might know as the face of Commander Shepard from Mass Effect, showed us that men’s fashion can be both tough and sophisticated. Meanwhile, Esther Cañadas, with her iconic pout and lightened brows, set the stage for the “model-off-duty” style that Gen Z is now rediscovering on resale sites like Vinted.