"This is always an interesting delivery," said the retail-minded Tracy Reese at her Garment District studio. "Waiting to wear something is outmoded, so we try to make clothes that are attractive for now but can last through the fall as a layering piece."

This time around, that meant thirties-inspired silhouettes that languidly hung on the body. "I wanted it to be sexy, but not tight," she said. Pleated, below-the-knee skirts were given a partially elastic waist for hidden ease, while Reese's popular full-skirted dresses looked airy and ballerina-like with dainty spaghetti straps. Prints are always a big story for the designer, and this season she took a traditionally spring-y motif—the tropical bird—and made it appropriate for fall by using muted colors. Even the deep blue floral print looked like it was more inspired by gemstones than the ocean. Reese used what she's calling a "checkerboard lace" in a series of separates and dresses. One look in particular—an oversize black top paired with a pencil skirt—caught the eye. The fabric was breezy enough to wear with strappy sandals in the summer, but structured enough to throw on with a turtleneck and a pair of serious single-sole heels come fall. For day-into-evening, Reese offered a black-and-metallic embroidered slipdress that captured exactly what she was trying to convey: It was sexy, but hung on the body in such a way that you could tell it was comfortable, too.

Reese's collections work again and again because she is so clearly designing what she likes and what she believes her customer will like, not what the industry dictates. Her confidence is a rare and admirable thing in a contemporary designer.