As the seasons progress, Jonathan Simkhai becomes more fearless. Fall 2014 was aggressively sexy, but in a sporty context. For instance, a pair of superwide-leg trousers—skate pants, okay?—were worn with a turtleneck cut out at the shoulders and under the rib cage, showing off a whole different sort of cleavage. "Under-boob action," he teased.

A cigar box covered in crocodile was an unlikely inspiration, but it got the young designer thinking about menswear. Along with the pinstripe looks that nodded to traditional suiting, he incorporated plenty of croc-embossed pieces, including a sleeveless turtleneck and matching mini, as well as a racerback dress with a zip front, which was done in a woven jacquard that almost shimmered. Simkhai is inching toward a runway show. This season at Milk Studios he used his presentation space to create a stage where models individually walked to the front and center to show off their wares. It was another indication that he's gaining confidence—and just might be ready for the big leagues.