Do you look terrible in a winter hat? Or just think you do?

Hat questions abound, such as, on an objective basis, who looks best in hats, and who should move to Florida?
Hat questions abound, such as, on an objective basis, who looks best in hats, and who should move to Florida?David L. Ryan/Globe Staff

Drizzling, cold, and raw, it was perfect hat weather. Well, for some.

“I don’t like my face when I have a hat on,” said Tom Bennett, a digital sports journalist.

He was in Macy’s men’s department, surrounded byhats, a young man doomed by his “big head” to a life of cold ears.

Many Bostonians dread winter, but for some, the cold hits harder than others. They are people who appear normal to onlookers but who have convinced themselves there is something about their head or hair or face that makes them look horrible in a hat! Much worse than average!

Like many wrestling with hat-onset noggin dysmorphia (not a real diagnosis, but it should be), Bennett periodically thinks he has found the one hat that can save him, only to realize, after he’s removed the tags, that it, too, is unflattering.


“I’ve given up,” he said.

But wherever he looks, hat people are in his face.

There they are on Instagram, smiling in a selfie, hair cascading just so. At the office, confidently making a presentation in a cuffed beanie. At a party, laughing at some private joke, their pompom lending a festive note. Or maybe they’re outside, ice skating in a trapper hat, toasty and attractive.

For those who whip off their hats blocks before reaching the office or meeting a date, hat people’s cheerful proclamations feel like mockery.

“Hats are just fun,” said Nicole Haftel, a senior at Boston University.

“It’s just another excuse to accessorize and express oneself!” said Karen Fabbri, of KFF Consulting, which advises small businesses.

“I kept my hat on at the Elton John concert,” said Peggy Rose, a publicist. “I liked the look of it.”

On the other end of the hat-emotional-comfort spectrum live the folks forced to seek refuge in cheap jokes at their own expense, desperate stand-up comedians.


“I’m a nose with a hat on,” said Toni Friedman Lansbury, a freelance advertising copywriter.

“My head looks like a giant egg,” said writer Beth Jones.

“The Pillsbury Doughboy,” said Robert Casey, owner of Maggie Inc., the modeling agency.

It’s hard to say if all, most, or simply many hat challenges are in the person’s head, but as one observer — Mint Julep boutique co-owner Brooke Garber — put it: “The better you feel about yourself, with or without a hat, the better you’ll feel in a hat.”

And the worse people feel, she’s noticed, the crazier they often go when hat shopping. “You suggest they start with a basic hat, and next thing you know, they are leaving with the biggest pompom.”

But years of hat failure play with a person’s head, make her jump from hat to hat, sometimes landing on a beret, or a hat with braids, or a trapper hat, not a good look on anyone but models or actual trappers.

“The struggle is real,” said Jaimie Adler, of Lexington.

Her curly hair is so vulnerable to hats, Adler said, that once she’s got one on, she can’t take it off. “I look like ‘Weird Al’ Yankovic.”

Hat challenges are disappointing year-round — “I don’t even look cute in a baseball hat,” Lansbury said — but with winter’s higher stakes, a few questions need to be explored:

On an objective basis, who looks best in hats, and who should move to Florida?


Casey, the round-faced modeling agency owner, says people with heart-shaped faces are in luck, and people with round faces are not.

“The hat emphasizes the roundness,” he said. “It can take away definition and make you look heavier.”

Hats also work their evil by negating a feature that many women rely on to feel attractive — their hair, specifically as it frames their face, said Vivian Diller, a clinical psychologist who has consulted on the psychology of beauty.

“Women with perfect features can put on a hat and those features are emphasized,” she said. But everyone is clinging to their hair for help. Or trying to.

In Roslindale, Jocelyn Hutt describes herself in a hat as “all hat, glasses and chin.” But at age 62, she still believes the perfect hat is out there for her.

“It’s like the right lipstick, or shoes,” she said, noting she hasn’t located those, either. “If I could just find the right hat, it would change my life.”

It’s nice to think so, but even the hat people understand that life isn’t perfect, that you have to make the best of the hand you’ve been dealt, said Lauren Beckham Falcone, cohost of “The ROR Morning Show.”

“I am actually overly confident in a winter hat,” she said. “You know how [Sports Illustrated cover model] Camille Kostek’s body is made for a bikini? My giant melon is made for hats.

“It’s not the body lottery I had hoped to win,” she said, “but I’ll take it.


Beth Teitell can be reached at beth.teitell@globe.com. Follow her on Twitter @bethteitell.