“I firmly believe,” actress Bette Midler once said, “that with the right footwear one can rule the world.” But when your world is winter in Maine, it’s another personal accessory that becomes crucial: the hat.

And not just to keep heat from escaping from our bodies, either. Though of course, they certainly do that. But winter toppers are also vital tools for self expression. They’re huge clues to who we are, what we do, and sometimes even how we think. So we asked a mix of Mainers who know a thing or two about each of the following hat styles what they say about those who don them.


The wool fisherman’s cap: This is the most classic Mainer’s hat, said Tara Knupp, vice president of merchandising and product development for Portland-based Sea Bags (seabags.com). “It’s no different than a favorite flannel shirt. It will be with you for a long time. My dad wears a fisherman’s hat that my great aunt knit for him probably in the early ’90s. What does it say about you? You’re functional, and you’ve lived here long enough to know you don’t leave home without it. And you likely have many in your drawer, like ragg wool socks.

A Bespolk pom pom hat. Photo by Winky Lewis

The pom-pom hat: “Hats with pom-poms have always been my favorite kind because they’re inherently a little silly and don’t take themselves too seriously – and neither do I,” said Liz Polkinghorn. She’s the owner of Bespolk hats (bespolk.com), who knits her pom-pom hats one by one in Falmouth and adorns them with cheeky sayings or one-word pronouncements knit right into them. “I believe fashion can be fun while also telling a story, and that’s what I’m trying to do.”


The hand-knit beanie: “As someone who loves cozy products that are high-quality, practical and versatile, I can tell you, knit beanies check all the boxes,” said ChappyWrap (chappywrap.com) President Christina Livada. She and her mother, Beth LaSala, run their stylish blankets company out of Cape Elizabeth. “Beanies blend beautiful design with practical warmth and are perfect for those long, cold winter days. They remind me of the Mainers that wear them – warm, go-with-the-flow, and always up for any kind of adventure.”


The trapper with ear flaps: “They’re basically the ankle-length puffer jacket of hats,” said Jennifer Bravo, who sells personal accessories and home decor at her brand new Portland shop, Viand Mercantile (viandmercantile.com). “Once you‘ve hit that level of warmth and comfort, you’re never going back. No matter how chic the style, the utility of the trapper hat will always stand out. Unless it’s on a small child with the sides tied up on top. … Then that’s just the cutest and cutest.”



Wool tweed caps or flat hats: These classics can be worn in all seasons, but are especially suited for autumn through spring, said Mark Reeth, who manages the shop On The Main in Ogunquit (onthemain.com), where tweed hats made by Mucros in Killarney, Ireland, are a consistent hit with guys of all ages. That said, the style doesn’t say any one thing about anyone, he suggests, because so many different folks grab them. “Women actually love them too,” he added. “They’re extremely versatile, and look great with a sport coat, khakis, a flannel shirt and jeans, or anything in between. And you definitely don’t need to be Irish to wear one.”

Alexandra Hall is a longtime New England lifestyle writer who lives in Maine.

This story was updated Dec. 14 to correct the relationship between Beth LaSala and Christina Livada of ChappyWrap. LaSala is Livada’s mother.

Only subscribers are eligible to post comments. Please subscribe or login first for digital access. Here’s why.

Use the form below to reset your password. When you've submitted your account email, we will send an email with a reset code.

filed under: