As a born-and-raised New Yorker, I feel well within my rights to say that when it comes to fall dressing in the city, the fashion crowd’s go-to outfit formula can be predictable. The look almost always starts with a strong foundation: a pair of jeans, specifically a silhouette that straddles the line between relaxed and slim-fitting with a lived-in, vintage-like denim wash. From there, the outfit builds with a long black wool coat and a black leather handbag.

Footwear is where styles typically vary, but they mainly are loafers, ankle boots, or ballet flats. For fall 2026, however, tastemakers are making a compelling case for swapping those choices for something different. Case in point: Olivia Munn’s latest ensemble.