An acquaintance recently DM'ed me a carousel of Audrey Hepburn's character Regina Lampert in the movie Charade with a simple proclamation: "It's you!" As I swiped through stills of the expressive character donning Hubert de Givenchy’s understated yet eye-catching costumes, I knew it was a compliment, to be sure, but what exactly about the images screamed me? I certainly don't claim to be as chic or elegant as the famed actress and style icon, but the answer proved less ephemeral: her cold weather garb, namely the hats.
After almost twenty years in New York, I'm no stranger to the city's brutal winters that make it difficult to justify dressing up (though I always manage to make it work). As a young adult, statement accessories were often at the forefront of my wardrobe (think: Jeffrey Campbell Litas or Schutz strappy heels—relics of my youth). These days, I've pared back, slowed down, and found that my true sartorial stride actually begins at the head rather than the toe, especially in the winter months.
A textured beanie. A ribbon-clad cap. A cobalt blue toque. When temperatures drop, you'll always find me with a hat in tow. Winter, though not typically lauded, presents an exciting opportunity to achieve the right balance of function and aesthetics. Erica Kim—a Toronto-based style creator and assistant professor—appreciates this idea. "Hats are practical yet feel so romantic to me because I associate them with historical novels and period fashion," she says.
Kim also acknowledges the practical realities of finding the perfect fit. "Not only do you have to consider the shape of your face, but there's also hat size, the shape of your head, and how you wear your hair and its color." She recommends visiting a hat shop to try on a range of styles if you can. "Once you find a few hat shapes you love, you can begin collecting them in different colors."
The same holds true for bookseller and writer Erin C. Messer: try them on in person, then wear them proudly. "In winter, I'd feel naked going out without a hat, even in comparatively mild San Francisco," she says. "My current favorites are berets in every color, especially jewel tones. I've been collecting them forever, but lately, my sources are vintage stores on the Haight and Etsy. It's quite cold where I work, and a beret feels right both outdoors and indoors. Plus, you can store them flat in a stack, and they take up very little room. I store mine in a cloth bin stacked by color."
For New York-based design and creative consultant Joyce Lee, color is just one part of the millinery allure. "I love how a hat can be a color or texture accent to a very simple look," she says. "I tend to wear neutral clothing and play around with a pop color or something really fluffy and oversized to give an unexpected detail to an outfit. It's fun to experiment with where the hat sits and how your hair frames your face." Los Angeles-based entrepreneur and lifestyle creator Candace Reels echoes this sentiment. "I love playing around with different shapes, textures, styles, and colors. Recently, my winter go-to has been a big red, furry hat. It seems intimidating to style a big red hat, but fashion is all about getting out of your comfort zone, taking risks, and standing out in a crowd of people."
Still, jumping into this sartorial moment isn't always simple. Lauren Cerand, a literary publicist in Baltimore, admits, "I wear one more often than not in my forties. I think before I did, I might have thought it a little costumey, but thinking of hats as purely functional (which they are), very useful when required, or to send a sartorial signal (which they do) helps make a habit of it." Yet, she loves "head-to-toe dressing and a gorgeous little hat often feels like the final touch," and notes, "When I lived in Florence to attend jewelry school for a year in 2019, there were so many beautiful [hats] in the vintage clothing shops I frequented—people are more dressed up there—that it was easy to begin by beginning, so to speak."
Stylist and creative consultant Caitlin Burke proposes another starting point. "For years, a wool or cashmere beanie has been the go-to head warmer for many in NYC, but I think balaclavas are the next natural progression," she explains. "Headwear quite literally tops off an outfit, and I found myself craving something still functional but a bit more interesting than a standard beanie. Balaclavas give you the same warmth but are a bit more unique and outfit-making. They add a bit of whimsy and also solve the problem of what to do with your hat once you get inside—since you can just pull down the hood!" (A few on her radar include Lemaire's Brushed Hood, Janessa Leone's Hazel Balaclava, and The Row's Everest Cashmere Ski Mask.)
And for those still on the fence, Dahana—an artist, content creator, and graphic designer—suggests not letting fear get in the way of trying a hat on for size. (At the very least, it might save you some time.) "When I don't have the energy to create an outfit, I just wear one of my many hats, random clothes, one of my long coats, and boom—I have my outfit for the day," she shares. "One day, someone stopped me to tell me that she loved my outfit, especially the beanie—that I crocheted—so I was even more proud. In my head, I was like, OMG, if only she knew that I'm almost in pajamas!"
Putting the personal back in personal style changes with the seasons, but I can't help but think of Lampert and many other complex heroines in wintry settings: a young Amy March in Greta Gerwig's Little Women bounding through the snow in tears wearing a chocolate brown fedora, Sex and the City's Carrie Bradshaw stepping out in a New Year's Eve blizzard wearing an unforgettable outfit topped with a sequin beanie. Winter feels different depending on where you live, but the women (real and fictional) I picture are often in motion: holding onto their hats to prevent them from blowing away, heading somewhere entirely themselves. In this way, what I've come to appreciate most about hats is how they call attention to our faces—and the raw emotion that's most notably on display during the darkest days of the year.
Style reminds us to celebrate this humanity, especially in the age of social media-driven movements (#hotgirlsummer, anyone?). In that vein, consider this my case for hat girl winter—less a trend, more a reminder to embrace all of life’s details, no matter the season.
Shop the Story:
Carpenter Hat
For a design-forward take on the beanie
Lauren Manoogian’s Carpenter Hat is easily the warmest winter hat I own—and one of the most versatile. Lee is also a fan. “It’s so densely knit and has structure, and because of that, it’s so warm; it is pure insulation,” she shares. “The shape of the top of the hat is unique, and I also love the wide cuff!”
Sheepskin Hat with Silk Tie
For an elegant outfit finish
We may have reached peak bow, but there's something to be said for a sleek ribbon detail. Cawley's sheepskin hats are stunners already, and this particular style maximizes function and fashion with a gorgeous silk tie. I have the Chalk/Ecru, but I'm also eyeing the Chocolate/Navy combo.
Brushed Beret
For a fun take on the beret
A beret was one of my earliest forays into hats. As a teenager, I was mad for the slouchy, knit berets often spotted on personal style blogs or the shelves of my local Urban Outfitters. Maria Stanley’s Brushed Beret is a fun take, and the material adds an interesting dimension to this beloved style. (I regularly wear her beanie in Plaid, and the weight is perfect for brisk days.)
White Rabbit Cashmere-blend Hood
For your inner child style
In the age of “girl dinner” and the like, there is something nostalgic about dressing for your inner child. Not to say that Sleeper’s White Rabbit Cashmere-blend Hood is by any means immature, but you can’t help but feel young at heart—and still incredibly chic—while sporting an adorable bunny on the side of your face.
Books Baseball Cap
For wearing your passions
It's never been easier to express yourself—and your passions. The rise of industry-related merch (think Sally Rooney's coveted Beautiful World, Where Are You? bucket hat) has swept across industries from publishing to food. For the former, might I recommend Pacific's "Books" Baseball cap? This casual outfit finish might just lead to a casual conversation (or several) about your latest reads…
Fleece Toques
For a pop of color
Colorblock your life and style with LLOYD’s various assortment of fleece toques. According to the brand’s site, LLOYD “produces everyday basics influenced by the slow fashion movement, periodically releasing seasonless garments and accessories made of high-quality natural fibers and deadstock fabrics.” As a proud owner of their blue toque, I feel anything but that while I’m wearing it.
Floppy Brim Fedora
For a timeless staple
Nothing screams classic hat style like a good fedora. The durability of rag & bone fedoras is unmatched. I have two from them that have lasted for almost a decade and have proven effective at warming and protecting—rain or shine.
Frayed Cordova Hat
For winter getaways
You can never go wrong with a Panama hat. I've had my eye on Sensi Studio for years, especially for winter getaways. Their attention to detail—think ribbons, tassels, ties!—makes them wearable art. Just take their Frayed Cordova hat, for instance. Talk about traveling in style.
Serpiente Knitted Crochet Hat
For gray winter days
There's something about crochet-anything that warms the soul. In the case of winter styling, Pardo's Serpiente knitted crochet hat also warms the head. Not to mention, the incredible design (knitted by hand!) provides an extra punch of color against gray winter skies.
Fleece Bonnet
For those still not entirely sold on hats
As Burke mentioned, “Balaclavas give you the same warmth but are a bit more unique and outfit-making.” In many ways, the same can be said for bonnets. Clyde’s Fleece Bonnet is simple yet striking, and for those who prize comfort, consider this your cozy-chic alternative.
"Sorry I Don't Work Here" Baseball Cap
For your day off
The saying goes that we work to live rather than live to work. But if you need an extra reminder on your day off, IDEA's "Sorry I Don't Work Here" Baseball Cap is the perfect rallying cry for your off-duty style. Pair it with an oversized coat and a pair of boots or sneakers, and there you have it. No apologies necessary.
Joy Hat
For pre-spring frolicking
Even for the biggest winter lovers, there comes a point in the season when all we want is just a little more warmth and sun. We can’t control the weather, but we can control how we feel. Sea’s Joy Hat is all in the name. The crochet bonnet’s dainty details give us a small dose of springtime style while functionally keeping us grounded—and ready to meet the day.
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