Never, you say?
"Wow, cool!" is just one of the many raves Jerry Bauman has heard as he strolls the city in one of the handmade Panama hats he's bought from Optimo, among the nation's premier hat shops.
"Wearing a hat is not a statement, it's an assertion. It's about your attitude to the world," says Bauman, 75, a CPA who never leaves home without one.
"I get a lot of compliments," says software engineer Curtis Tuckey, 47, as he sipped a drink at an outdoor cafe sporting the jaunty Panama hat he bought on a trip to Buenos Aires.
Wearing a hat comes naturally, Tuckey says, because he grew up on a farm in Michigan. "We always wore straw hats when we were working in fields in the summertime baling hay. My grandfather always wore a straw hat."
And unlike a baseball cap, the preferred hat of most men, "They give shade over the ears and the back of the neck," says Tuckey.
"It makes me feel elegant," observes Mark Warden, 73, the retired president of Richard J. Daley College, one of the City Colleges of Chicago, sporting a $1,200 Panama he, too, bought at Optimo, a 15-year-old shop in Chicago's Beverly neighborhood.
Warden's wife, Mary Beth Rebedeau, 54, a management consultant, says, "Men look so finished in a hat. It tops off how they look." And, yes, she frequently borrows her spouse's hat to top off her own look.
Entrepreneur Mil Ovan, 54, says strangers often tell him, "I wish I had the courage to wear that."
It's not really courage that's required, says Optimo shop owner and hatter Graham Thompson. It's having the will and the sense of style.
"Everybody who wants to wear a hat can wear a hat," says Thompson, 39, who often travels to Montecristi, Ecuador, where the world's finest straw is woven for the hats he sells, starting at $450.
"When you start wearing nice hats and you 'get it,' you cannot go back," says Thompson. "Once it becomes part of your life, you're a lifetime hat wearer."
Thompson, who started his business straight out of college, makes the distinction between confirmed hat wearers and the hipsters who pick up a small-brimmed topper for $15 at Target and are enjoying the fad for a couple months.
"Lots of younger customers, maybe their fathers didn't but their grandfathers did wear hats, and they're bringing them back into the family tradition," says Thompson, whose hats have appeared in films like "Public Enemies" on Johnny Depp's John Dillinger character.
I asked Thompson to come up with some adjectives that define a hat wearer, and he thought for a minute.
"Suave, cool, distinguished, a sense of adventure. It depends on who's wearing the hat and how they're wearing it," he says.
"When I see people wearing nice straw hats," says Thompson, "They're enjoying their summer more."
Choosing your hat
Pick what's comfortable and makes you feel confident.
Crown height and brim width should not overwhelm your face and build.
Fit the hat to your personality and personal style.
When to take it off?
When you're eating.
In the office.
In a crowded room.
In a place of worship.
In the rain or wind (if it's straw).