Eric McKissack, 59, is known for his financial savvy: He runs an investment management firm. But he also gets kudos for being one of the best-dressed men in Chicago. Whether it’s a bespoke three-piece suit for a board meeting or a cashmere Brunello Cucinelli tux for a gala at the Art Institute (he’s a trustee), McKissack appreciates exquisite fabrics and tailoring. “You wear well-made clothes; they don’t wear you,” he says.

He learned that lesson early in life. Growing up an only child in Nashville, he was influenced by a family of natty dressers, including an architect grandfather (who cofounded the country’s first registered African American architecture firm) and an art-collector uncle. Today, the Gold Coast 19th-century rowhouse that he shares with his wife, Cheryl, a marketing consultant, reveals his love of the finer things. For examples of art, objects, and apparel he loves, see below.

10 Things He Loves

BRUNELLO CUCINELLI TUXEDO ($6,895 for similar style, Brunello Cucinelli, 939 N. Rush St.)
“Navy makes you look a little—but not too—different.”

VALEXTRA BRIEFCASE ($3,419, Barneys New York, 15 E. Oak St.)
“It’s old Italian craftsmanship with contemporary design.”

CANDELABRA
“We go to Seattle often—my wife is from there. We bought this piece by an artist in residence at the Pilchuck Glass School.”

CIRE TRUDON CANDLE ($85, Jayson Home, 1885 N. Clybourn Ave.)
“I love this French candle maker’s scents and history.”

VINTAGE SAARINEN CHAIR ($3,447 for similar style, Design Within Reach, 1574 N. Kingsbury St.)
“It has the comfort of a wing chair, with a modern profile.”

BROADWOOD & SONS PIANO ($18,000 for similar style, antiquepianoshop.com)
“I was lucky to find it at an antique piano store in New York.”

JAEGER-LECOULTRE REVERSO WATCH ($15,400 for similar style, Marshall Pierce, 29 E. Madison St.)
“I’m a modest watch collector, and the Reverso is an icon. I like that it has an international time feature.”

GOLD & WOOD FRAMES ($825 for similar style, Glasses Ltd., 50 E. Oak St.)
“One side is horn; one side is wood. They are very comfortable.”

CHAKAIA BOOKER SCULPTURE (Prices for similar pieces by request, marlboroughgallery.com)
“Booker created an amazing sculpture out of rubber tires. It’s at the MCA now.”

MASERATI QUATTROPORTE SEDAN ($98,000 for 2013 model, Maserati Chicago, 834 N. Rush St.)
“This car is totally impractical for Chicago, but I love it.”

Photography: (Maserati) Courtesy of Maserati; (tuxedo, booker sculpture) Ratko Radojcic; (all others) Anna Knott