There are a few guiding elements at the core of BOSS. Those being passion, expertise, confidence, and craftsmanship. The brand’s Fall/Winter 2026 collection ensured that all those points were heard. But coming through the loudest was how easily confidence was expressed through construction.

Presented on the third day of Milan Fashion Week at Rubattino56, tailoring was the star of the show. The co-ed show drew celebrities like Meghann Fahy, Cat Burns, and Delilah Belle, with the womenswear portion centred on wearability. 

Through this lens, traditional tailoring moves beyond officewear. The pieces reemerge as multifaceted, taking up space in new arenas. We see suits styled with equestrian-inspired boots (some even thigh-high) and professional, work-like silhouettes paired with elbow-length gloves. These are looks that can be worn to the office but are also suitable for a dirty martini at happy hour. 

Playful details are sprinkled throughout, with double-belt layering and jackets featuring clip-on floral motifs. An eye-catching long red leather trench is layered over a white blouse with a dramatic neckline. Meanwhile, bags are buttery and smooth, with striking hardware—worn as clutches in the hand rather than over the shoulder to demonstrate versatility. 

At the heart of the collection is the energy the wearer brings to the clothes. It’s about how you make a piece truly your own. No matter the tailoring, the pieces become more powerful when imbued with personality. You’re the boss of the energy your clothes take on, and that, in itself, is an art.

Photos courtesy of BOSS.