Raf Simons cotton shirt, Valentino velvet and satin blazer, silk pocket square, Opening Ceremony cotton pants, Glenn silver bracelet, stainless steel and alligator watch, and Gucci velvet loafers

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