The Best Beanies and Other Winter Hats, According to Menswear Experts

(Bloomberg) -- By this time of the year, there’s a good chance you’ve already misplaced a winter hat or two. (No judgement.) So consider this as you ponder another purchase of this cold-weather essential: perhaps that hat wasn’t stylish enough, or soft enough, or warm enough to be memorable? 

That’s not a problem with the headgear below, selected by menswear experts who have considered the intricacies of beanies and basics longer and deeper than any normal person ever should. Below you’ll find their recommendations for the best winter hats, ones that balance utility (heat retention, moisture wicking) with aesthetics (cashmere, color) and price (from disposable to don’t you dare lose it) to keep you warm, but looking cool, well into spring. 

A Luxury Beanie

The Best Beanies and Other Winter Hats, According to Menswear Experts

Clockwise from left: Portolano ribbed cashmere beanie, $165, bergdorfgoodman.com; Loro Piana cashmere rib-knit beanie, $325, bergdorfgoodman.com; Andersen Andersen classic beanie, 500 Danish kroner ($76), andersen-andersen.com

Recommended by: Bruce Pask, men’s fashion director at Bergdorf Goodman and Neiman Marcus. He dresses the most stylish men in New York.

Pask loves the “simplicity” and “practical utility” of knit beanies or classic navy watch caps. He recommends luxury versions in cashmere by Loro Piana and Portolano, while his personal favorite, he says, are those in 100 percent merino wool by Andersen Andersen, “a Danish company that makes terrific fishing sweaters and knit beanies in a variety of great colors. There are also quite a few ways to wear them: rolled up high on the head, above the ears like those cool kids in the East End of London; folded up but worn down over your ears for maximum warmth; or unfolded, over the ears with the longer top sagging a bit in back. It all depends upon your personal style.” 

The Best Beanies and Other Winter Hats, According to Menswear Experts

Prada Padded Nylon Beanie, $360, matchesfashion.com

Recommended by: Matthew Henson, a stylist for musicians such as A$AP Rocky and The Weeknd.

“I’ve had some issues with losing all of my favorite knit beanies, so I resorted to buying all of my winter hats at one of my favorite places on Canal St,” says the New York-based Henson. “One afternoon, I was doing a pull at the Prada store on Broadway, and my magical saleswoman, Madison, brought out a nylon beanie which I’ve worn every day since. It fits my head perfectly, and since it’s pretty expensive, I’m mindful of its whereabouts and keep track of it.”

An All-Weather Fedora

The Best Beanies and Other Winter Hats, According to Menswear Experts

Goorin Radley felt fedora with earflaps, $150, goorin.com

Recommended by: Victoria Hitchcock, an image consultant for the tech titans of Silicon Valley.

“This retro-rad hat comes from Mrs. Maisel’s era,” says Hitchcock, who also name checks the company’s Slayer baseball cap ($30). Hidden fold-down earflaps and a wicking sweatband add versatile cold-weather functionality to the pizzaz of a fedora. “It will spruce up any look. Goorin has been around forever, headquartered in my stomping grounds of North Beach [in San Francisco], and consistently manages to outperform with impressive options that fit every head size I’ve ever come across.” 

A Basic Beanie

The Best Beanies and Other Winter Hats, According to Menswear Experts

Carhartt WIP Acrylic Watch Hat, $28, carhartt-wip.com

Recommended by: Fashion writer Steve Dool.

“My go-to winter hat for the last five years or so has been a somewhat obnoxiously neon orange beanie from the Parisian sneaker shop Starcow,” says Dool. “They aren't currently available to purchase online, so if a French holiday is not in the cards, the standard issue Carhartt acrylic watch hat is a pretty close approximation.”

The Best Beanies and Other Winter Hats, According to Menswear Experts

Dave’s New York Vintage Logo Beanie, $10, davesnewyork.com

Recommended by:  Justin Ocean, deputy luxury editor, Bloomberg Pursuits. 

If you looked up “beanie” in the dictionary, you’d very likely find these no-nonsense, affordable, knit acrylic hats. “They keep your head warm, come in a variety of colors, and are made in the U.S.A.,” says Ocean. “Dave’s New York is an iconic workwear store in the city, and I love to see who notices and recognizes Dave’s and mentions it. It’s like a secret club.” 

The Best Beanies and Other Winter Hats, According to Menswear Experts

Noah beanies, $30, noahny.com

Recommended by: Brian Trunzo, menswear forecaster at WGSN

“I like to go for something out there, a little noticeable, like something that’s neon-y,” says Trunzo, who buys a new beanie from Noah every season. “I like them to be fitted to my head. I don’t want it to be a head condom.” The streetwear brand is designed well and simply with a focus on quality materials, like Supreme for skaters who grew up (their designer was once with Supreme). And although Trunzo doesn’t like embellishments like pom-poms, a little flair never hurt anyone. Note: The official site is currently sold out, but retailers such as Ssense still have stock.

An Upgraded Baseball Cap

The Best Beanies and Other Winter Hats, According to Menswear Experts

Ermenegildo Zegna Navy Cashmere Baseball Cap, $395, zegna.com

Recommended by: Andrew Weitz, an image consultant based in Los Angeles

A choice for the less blustery winters of L.A., Weitz’s says his go-to hat this season is a cashmere baseball cap. “It keeps my head warm while still getting to wear a baseball hat rather than a beanie. It’s casual, chic, and stylish.” 

A Midrange Beanie

The Best Beanies and Other Winter Hats, According to Menswear Experts

Naadam Signature Ribbed Cashmere Beanie, $65, naadam.com

Recommended by: Hairstylist and salon owner Rodney Cutler.  

As you may have guessed from this list, a cashmere beanie is a warm, easy winter staple. But hair expert Cutler notes a big bonus: “cashmere doesn’t mess up your hair or cause static in the way that synthetic and wool blends can. I love this one from Naadam. It’s great quality at a great price.”

The Best Beanies and Other Winter Hats, According to Menswear Experts

Dertbag beanie, $40, dertbag.us or the Seam app

Recommended by: Jake Woolf, editorial director at shopping app Seam

“My go-to winter hat is this beanie from Dertbag, a streetwear label out of Connecticut that combines references from the worlds of hip-hop, prep, and the art scene all at once,” says Woolf. “That said, a big reason this beanie is so great is that it’s a really unique color for a winter hat—it isn’t often you see one in baby blue. Plus, I get a kick out of wearing a hat that says “dertbag” on it, front and center, when the style and color of it are anything but, well, dirty.” 

The Best Beanies and Other Winter Hats, According to Menswear Experts

Bloomingdale’s Ribbed Cashmere Beanie, $68, bloomingdales.com

Recommended by:  Garrett Munce, a freelance grooming consultant, writer and editor

“I always treat myself to a new cashmere beanie every winter, but then end up losing it about a week later,” says Munch, who instead offsets the loss by seeking out private label versions, like this one from Bloomingdale’s. “They're typically under $100, so I can stock up on several at once for the same price as a more expensive one. I’m a big fan of multiples—especially in cashmere.”

A Nylon Baseball Cap

The Best Beanies and Other Winter Hats, According to Menswear Experts

Polo Ralph Lauren Sportsmen Cap, $69.50, ralphlauren.com

Recommended by: Bobby Whigham, creative director of Pacsun, which brought SoCal skater style to the masses.  

While the West Coast-based Whigham says he always has a few brushed beanies in rotation (navy, grey, black, and the “essential” Carhartt safety orange, recommended above), in wetter weather, the season calls but for one thing: nylon. “It’s the perfect thing for the rain and fluctuating heat and unpredictable California weather. I love the terry cloth around the rim to keep the sunscreen out of my eyes and my head cool, and I love the pop of color in the back when I have sunglasses on,” he says. “It’ll be perfect for the transition to spring.”

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