Leo Dell’Orco, who has served as Giorgio Armani’s right-hand man for five decades, expressed deep disappointment over Italy’s failure to qualify for the World Cup, a sentiment grounded in his personal and professional ties to the nation’s football heritage. As head of menswear design and president of the Giorgio Armani Foundation, Dell’Orco’s career has been intricately linked with the intersection of fashion and sport, having been involved in the design of Italy’s national team kit under Armani’s direction.

Dell’Orco’s connection to Armani began unexpectedly when, at age 22, he and friends encountered the designer by chance during a holiday in Liguria. Invited to model in an upcoming menswear show, Dell’Orco found himself fitting perfectly as Armani’s fit model. Balancing this role with his day job as a technical draughtsman, he gradually integrated into the fashion house’s core team when Armani launched his independent label. Over time, Dell’Orco transitioned from fit model to key creative collaborator, working across menswear and womenswear divisions.

Throughout their working relationship, Dell’Orco recalls Armani as a leader with both a sharp sense of humor and an intense creative energy. Among the anecdotes shared is the presence of Armani’s bulldog, Gigi, whose unfortunate digestive issues often inspired lighthearted reproaches from the designer toward his impeccably dressed assistant.

A central focus for both Armani and Dell’Orco has been the jacket—a piece that Armani famously reimagined in the 1980s to blend sartorial elegance with comfort comparable to a cardigan. Dell’Orco emphasizes that this garment remains foundational in their design process, stating that every collection begins with the jacket.

Dell’Orco, now 73, has recently stepped into the role of leading Armani’s menswear design and creative direction. When asked about the challenge of succeeding a fashion icon, he responds with calm confidence, highlighting a philosophy of continuity paired with subtle innovation. He describes his style approach as “80 percent Armani and 20 percent Leo,” indicating a respectful evolution rather than a radical shift. This balance is reflected in his recent catwalk presentation held in the courtyard of the Armani palazzo, where he introduced elongated jackets and narrower trousers to subtly modernize the silhouette while maintaining the brand’s signature elegance.

Beyond clothing, Dell’Orco envisions extending Armani’s influence further into lifestyle domains, including hospitality. He foresees growth in the Armani Hotels portfolio, which currently includes properties in Milan and Dubai. Among his creative experiments for the runway was the inclusion of hats, an element he felt was consistent with Armani’s tradition yet offered room for playful expression.

Dell’Orco also reminisced about Armani’s previous collaborations with prominent football figures, including England captain David Beckham. Notably, Armani designed a fluid navy blue jacket for the England team, nicknamed “the Beckham,” underscoring the brand’s longstanding engagement with high-profile sporting ambassadors.

Despite changes in leadership and subtle shifts in design, Dell’Orco aims to preserve the essence of the Armani brand—valuing simplicity, elegance, and timeless style over ephemeral trends. As both a passionate football fan and seasoned designer, Dell’Orco embodies a bridge between Armani’s heritage and its future trajectory.