Ermenegildo Zegna Australian suit wool, E. Thomas brown plaid sport jacket wool, Maglia Francesco umbrella, Goorin Bros. Pebo’s Ghost hat, Randolph Engineering aviator sunglasses, vintage book, Kiton handmade calf leather shoes, Erreghe matte croc belt, Haberdash silk pocket square and dress shirt, and Carrot & Gibbs handmade silk bow tie

1 Ermenegildo Zegna Australian wool, $2,850 for a suit, and E. Thomas brown plaid wool, $1,900 for a sport jacket, at Richard Bennett Custom Tailors and Shirtmakers, 175 W. Jackson Blvd.; 312-913-1100.

2 Maglia Francesco umbrella, $227, at Shrine, 47 E. Oak St.; 312-675-2105, shrinestyle.com.

3, 5, and 10 Goorin Bros. Pebo’s Ghost hat, $45, Randolph Engineering aviator sunglasses, $99, and vintage book, from $5, at Isle of Man, 3856 N. Lincoln Ave.; 773-697-8035, iomstyle.com.

4 and 9 Kiton handmade calf leather shoes, $2,900, and Erreghe matte croc belt, $595, at George Greene, 49 E. Oak St.; 312-654-2490.

6 and 7 Haberdash silk pocket square, $45, and dress shirt, $158, at Haberdash, 1350 N. Wells St.; 312-440-1300, haberdashmen.com.

8 Carrot & Gibbs handmade silk bow tie, $70, at Neiman Marcus, 737 N. Michigan Ave.; neimanmarcus.com.

 

Photograph: Anna Knott