Bridget Maiellaro

The Old Town boutique Haberdash—one of the city’s few dedicated men’s shops—is opening a second location in River North in October. “We’re looking for a higher-profile spot that can put us on the map,” says Jerry Kamhi, who co-owns the shop with Adam Beltzman. “We used to be more about trend lines; now we’re a complete modern-day men’s store,” says Beltzman. Shoppers will find trendy attire from Rag & Bone and Hugo Boss alongside traditional apparel from the likes of Woolrich and Wolverine. This fall, look for Rag & Bone slub jersey henleys ($140), Woolrich cotton plaid shirts ($135), and Wolverine 1000 Mile Addison boots ($350). 1350 N. Wells St., 312-440-1300, and 607 N. State St., haberdashmen.com. Read more