Brothers Matthew and Alex Orley first met Samantha Florence at summer camp when they were still in elementary school. Two decades later, Samantha and Matthew are engaged. But their enduring connection isn't purely personal. In 2012, the trio launched Orley, a quirky knitwear line for men. Last season, they ventured into full-blown ready-to-wear, offering shirting and cotton trousers alongside sweaters and knitted sweatpants.

For Fall, the look is nostalgic—colors like rust, taupe, and brown are used on retro ski silhouettes—and it's fitting, given the team's wide-eyed, earnest attitude about clothes. "Last season was lush, romantic. This season is more linear and angular than what we've done in the past," said Alex at the Wednesday afternoon presentation. "It's our take on city dressing."

Albeit a city crowded with hundreds of Richie Tenenbaums. From the chevron-printed gloves to the red leather tie to the taupe button-up made from dead-stock Japanese silk cashmere, these are pieces that would speak to Wes Anderson's retired tennis champ. But the most successful styles were those featuring an Art Nouveau pattern inspired by the work of Eliel Saarinen. The Finnish architect designed the Michigan boarding school Cranbrook, which the Orley boys both attended. From a knit jacquard scarf to a woven cotton shirt, that nod to their early years felt personal and special. Sometimes, looking back can push a brand forward.