Getting your Trinity Audio player ready...
A cotton pocket square from J.Crew, Paul Smith cotton pocket square, Drake's cotton pocket square, silk twill pocket square, and a cotton pocket square from Brooks Brothers
Photo: Erika Dufour

Clockwise from top left:

  • Cotton pocket square, $50, J.Crew, 900 N. Michigan Ave.
  • Paul Smith cotton pocket square, $60, Apartment Number 9, 1804 N. Damen Ave.

More Top Picks Best Letter Trays

  • Silk twill pocket square, $150, Hermès, 25 E. Oak St.
  • Cotton pocket square, $20, Brooks Brothers, 4999 Old Orchard Center, Skokie.