Raf Simons cotton shirt, $306, Gallery Aesthete, 46 E. Oak St. Valentino velvet and satin blazer, $1,850. mrporter.com. Silk pocket square, $40, Brooks Brothers, 713 N. Michigan Ave. Opening Ceremony cotton pants, $330, and Glenn silver bracelet, $1,150, Independence, 47 E. Oak St. Stainless steel and alligator watch, $3,340, Montblanc, 900 N. Michigan Ave. Gucci velvet loafers, $550, Nordstrom, 55 E. Grand Ave.
Photograph: Anna Knott; Styling: Heiji Choy Black; Model: Matt Schur; Location: Trenchermen