After a lifetime of reporting on fashion, I’ve seen hundreds upon hundreds of trends.
It happens each fashion week, season after season, as a phalanx of long-legged supermodels parade across catwalks. New promises from designers and magazine editors are made. They swear that this one style or this one color (“puce is the new black!”) will be what everyone is wearing—the key to unlocking our personal style and becoming a fashionista that will part party-crowds and provoke a murmured chorus of “she looks great” from wide-eyed bystanders.
Those trends come and go. And then it’s on to the next fad, chasing style in a Möbius strip.
But fear not—I’m going to let you in on a little fashion secret, and you can skip out on all that future trend-chasing. Here’s what I’ve learned in my lifetime as a fashion writer. There is one sartorial move to master that operates outside all those blink-and-it’s-gone crazes. A great felt hat.
The power of a women’s felt hat is limitless. Unlike straw hats for women, which are more cute and casual, felt hats can be formal or informal, serious or fun, dark or light. But whatever your aesthetic, the addition of a great hat will solidify and elevate any outfit. So much so that you never have to worry about being in style—with a great hat, you’re trend proof.
Ready to dip into the unstoppable charisma of a hat? Follow along to learn how to style a women’s wool hat. Below, we’ve found 16 modern examples of how to wear a chic topper, from beginner level all the way up to expert. From New York Fashion Week trends, to red carpet moments, to cool-girl streetwear ensembles. This is your master class in how to wear a hat.
Try It: Embrace Felt Hat Duality
Perhaps the easiest way for a woman to wear a felt hat is to lean into the traditionally masculine aesthetic of Humphrey Bogart’s favorite hat, the fedora.
No stranger to competing archetypes herself, NASA scientist slash pageant queen Sarah Adewumi demonstrated this duality with her New York Fashion Week outfit. She split her look into a harmonious masculine/feminine combination.
Adewumi paired her women’s wide brim wool felt hat and blazer—traditional menswear pieces—with a cinched waist and ultra-femme white patent leather boots and bag. Follow her cool-girl blueprint whenever you need to make a splash.
Try It: Free Spirit Fedora Hat
Yes, it’s true: a wool fedora hat can telegraph Bohemian artistry!
Pair this gangster hat with an outfit featuring candy colors and eclectic details. This model at Milan Fashion Week wears paisley patterned pants, embroidery details, and leather sandals.
Make sure to watch the sunset as Stevie Nicks sings “Landslide” on your old, battered record player for the full effect.
Try It: Ultra-Posh Pajama Jam Hat
A mens fedora is typically worn with a classically tailored broad-shouldered wool suit.
But why not subvert expectations by wearing a women’s felt fedora with a suit of silk pajamas? It’s an unexpected move, but it will work if you keep your pajama set bright, bold, and luxurious.
Make sure you spring for the full set of silk pajamas in a rich hue or pattern. Need a suggestion?
We love the ultra-luxe pajama sets from Seoul brand Happiestness which boast the most beautiful pairs and are made from 100% pure mulberry silk. The rare silk is the highest quality that exists. It is created when the silkworms of the Bombyx mori moths are fed only mulberry leaves.
As demonstrated by this model at Milan Fashion Week, bonus points must be awarded to those who match their fedora and hat band to the exact same robin’s egg blue shade as their chic jammies.
Try It: Level-Up Your Weekend Basics
Just because it’s a hot day doesn’t mean you have to wear summer hats.
A crisp, structured felt hat is like a magic wand. Throw one on with whatever you’re wearing, and you instantly look like you have it all figured out.
Want respect? Wear a hat.
Social justice advocate Nikki Porcher demonstrates the instant-elevating power of a smart hat. Separately, all of Porcher’s pieces outside of her black felt topper are solidly casual: the oversized t-shirt, artfully torn jean shorts, and open-toed sandals.
When those weekend-ready pieces are topped with a classic structured hat, the outfit instantly veers into party-perfect territory.
Try It: Gray Is Your New Neutral
The easiest way to freshen up your outfit: Don’t reach for your typical women’s black newsboy cap. Instead, try the dapper topper in the rich, but neutral shade of dove gray.
Take, for example, Yoko Ono’s eclectic-but-chic look for a screening of “GasLand” in London.
The artist paired rebellious sartorial favorites of dark sunglasses and a leather jacket with an elegant, smoky-hued fedora just the right size for an unexpected twist.
Rather than follow the bucket hat trend like everyone else, she sets them herself
Try It: Embroidered Hat Embellishments
Teach an old brown hat new tricks by adding a colorful, hand-embroidered embellishment like this beauty we spotted at Miami’s La Plage Swim Week.
A bright and bold parrot is an excellent choice for a sunshine-soaked vacation locale like Miami (consider this your permission to wear felt hats in the summer). But the possibilities are limitless when it comes to personalizing your hat.
Try something simpler, like your initials, for monogram minimalists or something whimsical, like your home state’s official flower, for a dose of romantic nostalgia.
Try It: Dress Up Your Hat Band
Ears, necks, wrists, and fingers get all the baubles, but won’t someone consider the Western wear too?
Your hat deserves jewelry too!
Whether its straw or felt, adorn your women’s cowboy hat with a special band of painted leather, silver (as demonstrated by Evelyn Menin and Christina Getty in Aspen), gold, or diamonds if you’re feeling eccentric.
Lean into it.
The ranchers will whisper, and that’s how Western legends get sparked, you Felt Cowgirl, you.
Try It: Modern Dandy Hat
Annagiulia Firenze’s use of hats is always an endless source of inspiration for us when it comes to our personal style. The Italian design house has a way of dressing their models to make them feel both modern and traditional—like jet-setting time-travelers who have been collecting their wardrobes piece by piece as they zigzag through time zones.
This model’s modern dandy look calls to us thanks to the fresh and femme deconstructed suiting, pulled together by a classic felt flat cap.
To create the aesthetic, keep the blouse Bohemian and layer on the structured suiting separates. Finally, pull that scally wool brim over your eyes for an instant dose of intrigue.
Try It: Monochromatic Black Hat, Beginner Level
Does a hat belong on a red carpet?
Take a cue from two-time British Olympian Aimee Fuller. She matched her black cocktail dress to her sharp and chic fedora. And she protected her face from the harsh sunlight on the red carpet at the London premiere of “Jungle Cruise.”
Her monochromatic look puts this hat brim tipper squarely on the best dressed woman’s list.
Try It: Monochromatic Black, Expert Level
Once you’ve mastered beginner-level monochromatic, kick it (way) up like supermodel Cindy Bruna did for this UNICEF event in Capri, Italy. Bruna looks phenomenal, of course, in a black bodysuit and coat.
But what brings her look into gasp-worthy territory is the custom-made felt hat from Ukrainian milliner Ruslan Baginskiy. She is the moment thanks to the unexpected, dangerously sexy hat.
If you’re bold enough to copy Cindy’s bolero look, the key is to really go there.
No hesitating: make sure your ladies wide brim boater hat is extra wide, your heels are extra high, and pile on the diamonds, darling.
Try It: Bright & Bold Maximalism
Legend has it that you are physically unable to be in a bad mood while wearing heart-shaped sunnies and a women’s wide brim pink fedora hat.
Take it from Tara and ditch that old brown hat.
Tara Reid proved the maximalist mantra is correct while at an art exhibit in LA. She even tripled-down on her endorphin boosting accessories by wearing them with a sequin dress—and we applaud the commitment to flash.
Try It: Subversive Black Hat Fashionista
I can only imagine the murmurs and wide eyes that followed Brazilian actress Bárbara Paz everywhere she went the night that she showed up to the Venice International Film Festival wearing this.
“Unexpected” is the first word that comes to mind and “iconic” is the second. The women must have blushed and cursed themselves for reaching for the same old gown. And the men must have looked down at their own tuxedos and wished they looked as good as Paz did.
And, yes, the hat makes the outfit. Paz’s tuxedo is a subversive red carpet choice. But the oversize, extra wide-brimmed women’s fedora (slanted at the perfect angle) with a big city flair is what solidifies her as a permanent fixture on the best dressed list.
Try It: Rainbow Bright Felt Hat
Get inspired by the LGBTQIA+ Pride marches held around the world each summer.
Swap out your neutral-shade rancher style felt hat for one bursting with colors. All hats look good in rainbow hues, but we really love how the classic cowboy hat transforms when it’s soaked in life-affirming colors.
Don’t worry about finding the party. When you wear a rainbow hat, the party will find you.
Try It: Full Goddess Mode (Cape Included)
Go full goddess. We dare you.
While not for the faint of heart, there’s no question that this look is a full serve. Pair a white gown with a white cape and a white top hat and oversize brim for a look that is wholly dramatic. Sure, a jewel-encrusted crown would have been a viable red carpet choice but a wide-brimmed women’s wool felt hat, that’s the powerful pick.
People will stare at your outfit no matter what you wear—you might as well give them something worth talking about.
Try It: Downtown Dress, Uptown Women’s Wool Hat
A friendly reminder from fashion journalist Kryselle Cabral: a black hat shouldn’t wait for black tie. Take your formal fedora downtown by pairing it with decidedly cool pieces (trust us, you’ll be turning heads all night). Cabral paired her felt topper with a body-con dress, vampire-red glasses, a chubby fur coat, and patent leather boots. The result? A perfect outfit.
Try It: Too Sweet Is Never Enough
There’s something satisfying about ladylike dressing as you hail a cab to shop.
It’s the details, isn’t it?
Committing to an ultra-femme, full-tea-service look means you can pile on all the twee accessories you want with no reservations.
Emily Roberts demonstrates the candy-coated power of a sweet outfit while attending the Frauen 100 in Berlin this summer.
Roberts paired a waist-whittling corset with an A-line skirt in a matching bubblegum pink hue, wrist length white gloves, a tidy shoulder bag, rose-colored glasses, and the perfect Parisian wool beret.
Women’s Felt Hats Drops Here
If you buy one thing this season: make it a felt or wool hat. It is the most flattering, most trend-proof accessory of the 20th century. There’s no arguing with that fact.
Judy Garland wore it. Diane Keaton wore it. Jennifer Aniston wore it. Women have looked wonderful in a hat, generation after generation. And they still do.
And, yes, I’m talking about you specifically.