Raymond Hudd has no customers in his north-side hat shop, and he’s not expecting a rush anytime soon. “No one dresses up anymore,” he says, shrugging. “It’s not like it used to be.”

Give the 70-year-old Hudd an opening–almost any fashion faux pas will do–and chances are he’ll launch into a peevish dissertation on the hippie movement. “They just didn’t get it,” he says, pacing the cramped but tidy storefront that’s filled with odd-shaped derbies, bonnets, and fedoras. “They didn’t understand, and now their kids don’t understand.”

The way he sees it, there’s little to distinguish those in today’s army of trendsetters. Grungers, preppies, slackers, hipsters, professionals, and punkers are all in drab. And that makes the job of a milliner tricky. “Women love to try on hats,” he says. “That’s why they come in here. The woman in them is dying to come out.” But they don’t buy hats like they used to.

“You look beautiful,” Hudd gushes at a young brunette who’s decked out in a business outfit. She sets a sleek, fuchsia Hudd original on her head. Doffing this creation for another, she parades in front of the shop’s full-length mirror. “Oh, I love them,” she says. “But I have no place to wear them.”

“But you can wear them anywhere,” he pleads, then launches into his lecture on how hippies destroyed hat couture.

A look of intrigued bewilderment settles on the woman’s face. She buys a harmless tan beret and apologetically promises to return.

“When women come in my shop today I have to tell them where the tag goes,” Hudd complains. “It wasn’t always that way.”

He gazes up at a gallery of framed press clippings from the 50s and early 60s that nearly cover the wall behind the counter. “Those were the hat days,” he says with a twinkle. “A time when women weren’t afraid to look beautiful. Before femininity was hidden. Before the hippies changed it all.”

At 18 Hudd left his family’s farm in Michigan and journeyed to Chicago, where he discovered the concept of fashion while working as a window-display designer at a Loop department store. “No one had to teach me,” he asserts. “I observed it.”

Six years later, in 1950, he had scraped together enough money to open his own high-style milliner’s shop at Clark and Division.

With his eye on the nouveau riche, he soon moved to 40 E. Oak, where his business thrived for 20 years. He says his eye-popping window displays prompted a sight-seeing bus to include his shop among its regular stops. “My motto was ‘If you don’t know me, you’ll see me.'”

By the late 50s Hudd was one of the city’s costume kings, designing hats for fashion-show luncheons at grand hotels like the Edgewater and the Drake. Phyllis Diller became a close friend and admirer, dropping by his shop regularly and shooting faces at window-shoppers.

“It was wonderful,” he says with a smile and a disconcerted glance at his pilling green sweater and weathered gray slacks. “Women had a hat for work, a hat for church, a hat for cocktail and dinner parties. It was the crowning jewel of a woman.” He drops his voice to a whisper so as not to attract the attention of another female customer and says women then adopted an “if men don’t have to wear them then neither do we” attitude. “The children of that generation used to play dress up as little girls, and now that they’re adults they dress like little boys.”

A woman enters the shop gripping a man’s straw hat, searching for a band to wrap around it. Hudd says gently, “There aren’t too many shops like this around, let alone one for men.” Then he asks who wears the hat.

“Oh, it’s my husband’s hat,” she says abruptly.

“Well, there used to be plenty of fine men’s shops back when it was popular to dress in style,” Hudd begins. But the woman is dashing back out to her double-parked car. “She probably wears that thing,” he sighs.

By 1970 Hudd’s business had been run off the fancy stretch of Oak Street by “ragtag” outlets. He proudly says he was one of the last to leave. Shunning offers in New York and Hollywood, he spent the next ten years working as a wholesaler to major department stores, including Marshall Field.

But in 1981, convinced he still had loyal customers, he defied fashion and opened his current shop at 2545 N. Clark, where the sign says only Raymond Hudd. The stubborn throwbacks come, but most customers are just looking.

Hudd does have a sideline– “head art”–which he started back in his heyday, when a TV weather reporter commissioned him to make hats with a sun, a cloud, a lightning bolt to use as props during the nightly forecasts. “It was pretty demanding work,” Hudd says. He steps behind the curtain at the rear of his shop, brings out a glittering silver sphere, and proudly sets it on his head. “Guess what this is made out of?” he asks, pointing to the dome. “It’s a bowl from my kitchen.”

He spends a lot of time digging up objects like kitchen utensils to mold into these fantastical helmets, which have gained him the monikers the Mahatma of Hats and the Mad Hatter of the Midwest. He has at least a couple dozen, including a pillbox inspired by the mid-80s Tylenol scare that has two mice tumbling over a medicine bottle and tiny red and white capsules caught in a lacy veil; an Ollie North top hat with a dangling collage of shredded paper and dollar bills; and a derby with a pig and the Spam logo mounted on it. All are meant to be displayed rather than worn. One local gallery actually gave them a brief exhibit. Rarely, he says, are they sold.

But even as he fiddles with one of these creations, he can’t stop bemoaning the current state of fashion. “Men are starved for women in hats. Every man loves a feminine woman, and a woman wearing a hat defines her femininity.” He says he’s tried to keep the gracefulness of the 50s alive, then shrugs. “But I’m getting too old to care.”

Just then he spots another window-shopper eyeing his hats. He smiles and whispers, “Feminine florals are coming back, you know?”

Art accompanying story in printed newspaper (not available in this archive): Photos/Mike Tappin.