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What Are the Most Stylish Winter Hats?

Photo-Illustration: The Strategist; Photos: Retailers

Four years have passed since we said Carhartt had reached “peak beanie.” You can’t go a block without seeing the yellow-orange logo. At this point, they’re akin to the black puffer: It’s the safe and easy choice, neither trendsetting nor super-fashionable. So we wanted to figure out what, if any, winter hat is the new status symbol: What comes next in a post-Carhartt world?

When I reached out to Anush Mirbegian, creative director of accessories at Fashion Snoops, she told me that knitwear is on the upswing. This emerged from “the desire for coziness and comfort during and nearly post-pandemic, as well as some sustainable innovations in the knitwear sector,” she says. Her theory proved to be correct after I surveyed 13 other stylish folks about the winter hats they’re seeing and wearing lately. Knitwear was seen across the board, from bucket hats and balaclavas to beanies and bonnets. But we also saw some outliers, which we included for good measure. Read on to learn exactly which winter toppers our panel of fashionable folks says are the next status hats.

Bucket hats

While bucket hats have been on trend for a while now, they’re typically reserved for warmer months. But a recent knitwear revival has primed us for faux fur and other cozy versions of this staple.

Emily Dawn Long’s bucket hat stood out as the only one with three recommendations (and multiple in-person sightings). It’s slouchy, like a bucket hat–beanie mash-up, so it makes sense that this particular style would make the cold-weather crossover. Strategist editor Maxine Builder pointed out that Outdoor Voices founder Ty Haney has one herself and that she’s seen it pop up around Williamsburg. (I can also attest to this, after seeing one sitting in the window of the newly opened, buzzy JuneShine taproom on the corner of 8th and Berry Streets and on several L train passengers.)

Kule content and marketing manager Elizabeth Tamkin and artist Janie Korn also brought up the hat. Tamkin likes the fuzzier one for winter, while Korn, who’s “typically hat agnostic,” says the Hat Named Wanda “really changed the game for me … It’s an all-terrain, cool-person hat. I also love wearing it right after washing my hair because it shapes my bangs perfectly into place — a technique I call ‘hair training.’”

Tamkin said this wool bucket with a cable-knit pattern shows how the silhouette has been winterized.

Elana Fishman, style editor at “Page Six,” argues that faux-fur bucket hats are “definitely the winter hat of the year,” playing off of the “Y2K vibe everyone’s after right now.” (Though she notes that it isn’t her personal style per se.) Fishman cites Rihanna as one of the first celebrities to usher in the “high-fashion Muppet” look, with other celebrities like Hailey Bieber, Megan Fox, and Bella Hadid following suit. She adds that it’s an easy trend to hop on since there are lots of under-$50 options and “countless colors” to choose from.

Food52’s brand marketing manager, Rilka Noel, says her reversible Coming of Age bucket hat is “a bit more unexpected than just a classic beanie.” While she says it “definitely [plays off] the whole annoying Y2K revival,” this is a way to make it “fun and tasteful and not overly trendy.”


Balaclavas were the second-most-mentioned hat on our list. Fun knits are the go-to (as opposed to sporty, utilitarian versions).

This balaclava with pom-poms and embroidered multicolored flowers was recommended by Mirbegian. Its decorative elements “speak to our collective desire for nostalgia and crafting,” which she says are two emerging trends.

Noel says she has spotted colorful balaclavas made with elevated materials like cashmere and wool around the city. She’s had her eye on Loeffler Randall’s and Lisa Yang’s cashmere balaclavas. She’s into the bright green and blue colorways specifically because they’d “make the classic New York–uniform black puffer jacket a bit more exciting.”

Stylist Lilli Millhiser recommends checking out & Other Stories for nice balaclavas at a more affordable price. While the one she bought is no longer available, the brand offers a couple of neutral options and this bright pink one.

For days in New York that aren’t “cute cold but actually wet and disgusting,” Noel reaches for her North Face. The water-repellent balaclava is “a little sporty and technical, but still looks kind of cool.”


Mirbegian says that bonnets were an emerging style during last year’s runway shows, from brands like Max Mara in Milan and Yuhan Wang and Eudon Choi in London. Three other stylish folks also mentioned bonnets, which might speak to the beginning of a more micro-trend.

According to Tamkin, quilted bonnets “became really trendy last year but are still going strong” and cites influencer and fashion blogger Patricia Sañes as someone she saw wearing one. Tamkin also notes the versatility and convenience of it: “You can wear them as a scarf or hat and they’re adjustable — you just tie it under your chin as tight as you want depending on wind strength!” She personally owns this Ienki Ienki orange number made with goose-down feathers.

Artist Anna Sergeeva, who is studying at Pratt Institute, says earmuffs have surpassed beanies on campus. “The other day after class I saw basically everyone wearing earmuffs — maybe like one beanie per ten earmuffs,” she says. In her Bed-Stuy neighborhood, she’s spotted lots of bonnets, similar to this faux-fur one from Ruslan Baginskiy.

[Editor’s note: This bonnet hat is not currently in stock, but you Ruslan Baginskiy will make one for you in 14 business days, according to the product page.]

And the knitwear trend continues, as Korn has been “dreaming” of Ella Emhoff’s bunny bonnet. She “loves how whimsical and playful it is and how it finishes with a big sweet bow around the neck.” Each bonnet is customizable and hand-knit by Emhoff herself in Brooklyn.

[Editor’s note: Commissions for this bonnet are currently closed. Be sure to check back on Emhoff’s website for updates.]


While beanies may not be as trendy at the moment, they’re not going anywhere.

Both Kiran Jade, founder of Wolven, and Millhiser mentioned chunkier handknit options. (Millhiser says she was directly influenced by Diana Ross’s at the beginning of Mahogany.) And Mirbegian pointed us to this even chunkier cable knit hat.

According to writer Lee Tilghman, this specific Viking Blue Patagonia beanie has been popping up in her Cobble Hill neighborhood. She predicts it having a “big moment” this winter because it’s a “mix of ’70s nostalgia and preppy.”

Lastly, content creator Phoebe “Pojo” Joseph suggests going with neutral beanies but looking for limited-release drops. She specifically pointed to the ALD x New Balance and Anna Sui x Alice in Wonderland beanies, both of which can be found secondhand (just be sure they have all of their tags, she adds).

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What Are the Most Stylish Winter Hats This Year?