There was no easing into his new role at Trussardi for incoming creative director Umit Benan. The Italian brand is celebrating its centennial this year. To mark the occasion, the label held a full-scale women's runway show—in a clear tent in the middle of Milan's fourteenth-century Castello Sforzesco, no less. Afterward, there were food and wine and an alfresco dance party.

The pressure was really on Benan, especially when you consider menswear is this relatively young designer's first calling. On a very basic level, he's proven with the men's collections for his own label that he appreciates how people actually wear clothes, a talent that shouldn't be underestimated. In that regard, his first women's outing didn't disappoint, even though it might've been better appreciated in more intimate surroundings, where you could see its promising, everyday beauty close-up. The vast stage also seemed slightly at odds with the sort of evocative mise-en-scène the designer specializes in at his own presentations.

In a preview, Benan called his girl "the granddaughter of Annie Hall." As that suggests, there was a lot of men's tailoring—slightly oversize and boxy jackets, and pants that were high-waisted and full and cropped above the ankle. The trench with a crocodile collar was inspired by house founder Nicola Trussardi's original. It was typically smart of Benan to build on his menswear foundations in this way.

Trussardi is a leather-goods house first and foremost, so the models often carried two bags, a long-shoulder-strap style and a weekender or a backpack or a hard case in high-contrast black and white. (Travel, as the airplane seats assembled at the back of the runway suggested, was a theme here.) But Benan seemed more confident with the mix and match of his clothes. A good percentage of the looks incorporated at least three pieces. Our favorite: a red blazer that topped a slightly different shade of red button-down and rust-colored long shorts. It looked sophisticated but still easy, a combination a lot of women could get behind. It was an indication of what Benan can achieve if given full rein to explore his vision.