Unexpected Ways to Pick and Style Mens Felt Hats

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We’ve been playing it safe for almost two years now in every aspect of life. 

For months, fashion had been reduced to nothing more than matching sweat suits and above the waist dressing (in case of Zoom meeting). No stylish men’s felt hats have been worn during all those long, couch-bound quarantine days doing puzzles and binging Netflix. 

But now. 

Now, we’re back. 

It’s time to wake up from our elastic waist ennui and get back to the charisma-sparking, mood buoying power of style. 

Out of practice? That’s okay. 

It’s understandable—relatable even—if you often find yourself in front of your closet, staring blankly into the silk- and cotton-filled abyss, wondering how you managed to pull this off (every single day!) in 2019. 

For those in need of a little sartorial reminder of how fun it is to dress up, we’ve compiled a list of our favorite men’s hat trends. Specifically, men’s felt hats.

Think of these suggestions as fashion dares: fool-proof outfit formulas that are on trend and will give you the dose of confidence you need to face the world again, this time without the sweatpants.

Try It: Beret with Fur Ear Muffs

A model walks the runway wearing a felt beret for Louis Vuitton
PARIS, FRANCE: A model walks the runway wearing a felt beret during the Louis Vuitton Menswear Spring/Summer 2022 show as part of Paris Fashion Week on June 22, 2021. (Photo by Kristy Sparow/Getty Images)

The beret might be my personal favorite felt hat of all time for one simple reason: men look good in berets. Picassco did, while disrupting the art world in Paris. Hemingway did, while watching bulls run in Pamplona. The Guardian Angels did, while protecting 1980s New York City. Kim Taehyung did, while performing with BTS at Wembley Stadium, London. Men’s wool berets are a shortcut to style.

Pablo Picasso (1881 - 1973) in a felt beret, 1950s.
Portrait of Spanish-born artist Pablo Picasso (1881 – 1973) in a classic Parisian black wool beret, 1950s. (Photo by Hulton Archive/Getty Images)

Virgil Abloh embraced the timeless, stylish perfection of wool berets when he designed Louis Vuitton’s Spring Summer 2022 line. The sophisticated topper went full “cool guy” as Abloh reimagined the beret with Y2K aesthetics and bold streetwear pieces. Elevate your favorite grails and other streetwear pieces this fall by pairing them with a chic and sophisticated beret. 

Trust us: you’re going to love this fit. 

Try It: Expert-Level Beret

A racegoer attends Royal Ascot 2021 in a plaid, felt beret
ASCOT, ENGLAND: A racegoer attends Royal Ascot 2021 in a plaid, felt beret at Ascot Racecourse on June 15, 2021. (Photo by Samir Hussein/WireImage)

Now that you’ve mastered a basic wool beret, are you ready for the boss level? 

You don’t have to be a Scotsman to wear men’s felt hats. Your next fashion dare is to embrace the festooned beret. The chic topper becomes party-ready with the addition of a plume of feathers, a decorative brooch, or when rendered in a satisfying crisscross of plaid wool. Trepidatious about the loud topper? Keep the rest of your fit balanced by wearing sharply tailored wool suit (and prepare for the endless flood of compliments). 

Try It: Sexy Take on Western Hats

Fullout Cortland wearing a felt cowboy hat while attending Drive Change For BIPOC Creators
LOS ANGELES, CALIFORNIA: Fullout Cortland wearing a felt cowboy hat while attending the Logitech And Visionary Choreographer JaQuel Knight Drive Change For BIPOC Creators Through Copyright Protection And New Film on July 28, 2021. (Photo by Tommaso Boddi/Getty Images for Logitech)

Black Stetsons ain’t just western wear for cowboys, ranchers and rodeo hands. Over the past few decades, these hat has moved from a utilitarian item into the fashion world.

Even more recently, the cowboy aesthetic has evolved to a decidedly sexy realm. Thanks in part to ’00s pop icons like Britney Spears and, more recently, Lil Nas X, the cowboy hat is subversive. 

Celebrity choreographer and creative director Fullout Cortland is the perfect example of how to embrace the ultra-sexy new direction of cowboy hats.

His formula for a hot-as-lava look: layer on the jewelry, wear a sheer shirt (unbuttoned down to there), cowboy boots and make sure you never take off your hat.

Try It: Embrace Hipster Headgear

A model wearing a felt deerstalker hat at Milan Fashion Week
MILAN, ITALY: A model wearing a felt deerstalker hat attends the Nick Fouquet – Federico Curradi presentation at Milan Fashion Week on June 20, 2021. (Photo by Vittorio Zunino Celotto/Getty Images)

The deerstalker hat is one of those accessories so fabulous, if you know them by name, you’re not part of the mainstream.

It thrives in three opposing, niche groups (hunters, hipsters, and fictional detectives), but deserves a much, much, wider level of adoration.

Equal parts quirky and practical, the deerstalker hat injects an element of insta-sleuth into any outfit. But make sure you get the right size because fit really matters.

Try taking a crushable felt deerstalker out of the woods, like this model at Milan Fashion Week by wearing easy, casual-cool staples in a neutral palette that don’t compete with your hat. It should always be the star of your outfit. 

Try It: Expert-Level Deerstalker

A model walks the runway wearing a plaid felt deerstalker hat
ROME, ITALY: A model walks the runway wearing a plaid felt deerstalker hat at the Accademia Costume & Moda Fashion Show of Filippo Alimonti during Altaroma 2021 at Cinecitta Studios on July 07, 2021. (Photo by Elisabetta Villa/Getty Images) 

Take the deerstalker to the next level by embracing the Sherlock Holmes-ness of the classic men’s felt hat.

Once you’ve mastered wearing the quirky wool topper with neutrals, lean into the maximalism of double plaid, bright pops of color, and a stylized, modern brim like this model in the Altaroma 2021 fashion show in Rome. 

Basil Rathbone (1892 - 1967) wears a plaid felt deerstalker hat
British actor Basil Rathbone (1892 – 1967) wears a plaid felt deerstalker hat as fictional detective Sherlock Holmes, circa 1939. (Photo by Archive Photos/Getty Images)

Warning: this move is not for wallflowers. But if you want to be the most interesting person in the room without saying a word, embrace the coolness of the bold and brilliant deerstalker hat.

Try It: Far Out Felt Hats

Ramin Hajipour and Daelen Cory wear felt cowboy hats
LOS ANGELES, CALIFORNIA: Ramin Hajipour and Daelen Cory wear felt hats while attending the 26th Annual LA Art Show Opening Night Gala at Los Angeles Convention Center on July 29, 2021. (Photo by Kevin Winter/Getty Images)

Alexa: play “Bohemian Rhapsody”. 

Here’s proof positive that a serious, structured tan or black hat can be a part of a playfully Bohemian vibe. We love how Ramin Hajipour and Daelen Cory (seen here at the annual LA Art Show’s Opening Night Gala) stacked their looks with artful details and used a 10-gallon felt hat and black felt fedora to anchor their eccentric fits. The layered psychedelic prints, the veiled face mask, the statement glasses and stacked jewelry—their outfits are a groovy discordance, made harmonious by the structured felt hats.

Try It: Formal Clash

Sevyn Streeter and D-Nice, wearing a felt hat, attend the BET Awards
LOS ANGELES, CALIFORNIA: Sevyn Streeter and D-Nice, wearing a felt hat, attend the BET Awards 2021 at Microsoft Theater on June 27, 2021. (Photo by Paras Griffin/Getty Images for BET)

How to look like the most fascinating person in the room: 

First: Order a sharply tailored suit. 

Next: Get a gorgeous wide brim men’s felt fedora that clashes. 

Finally: Prepare for the receiving line that will want to shake your hand and tell you how great you look. 

Producer and rapper D-Nice looked ultra-dapper at this year’s BET Awards thanks to his structured suiting and felt fedora hat rendered in a gorgeous pacific blue hue. He looks great in his navy wool suit, of course, but the contrasting hat in a rich, saturated shade of blue elevates his outfit.

By purposely letting his blue felt fedora stand out, it takes on a regal, crown-like appearance. 

Try It: Monochromatic Millinery

Nile Rodgers wears a felt beret during The National Lottery\'s Team GB homecoming event
LONDON, ENGLAND: Nile Rodgers wears a felt beret during The National Lottery\’s Team GB homecoming event at the SSE Arena Wembley on August 15, 2021. (Photo by Gareth Cattermole/Getty Images for The National Lottery)

Singer-songwriter producer Nile Rodgers understands the power of a monochromatic hat moment. For The National Lottery’s Team GB homecoming event at Wembley Arena, the masterful producer pulled a masterful sartorial move by matching his felt hat to his suit. 

“My default headgear is a Kangol Bamboo beret that I color-coordinate with my outfit,” Rodgers told The Guardian. “I love clothes. Every time I get dressed, even to walk around the house, I feel like I’m playing dress-up.” 

Take it from Nile Rodgers: the true power of a great felt hat is the instant confidence boost. 

Try It: Elevate a Casual Felt Hat

Troy Kotsur wears a wool scally cap while attending the
WEST HOLLYWOOD, CALIFORNIA: Troy Kotsur wears a wool scally cap while attending the \”CODA\” Los Angeles photo call at The London West Hollywood at Beverly Hills on July 30, 2021. (Photo by Rodin Eckenroth/Getty Images)

Can a scally cap show up to a red carpet? Absolutely! Troy Kotsur proves that you can mix and match a casual hat with more formal outfits. For a press event and photo call in Beverly Hills, the actor and director wore a dark wool scally cap with a sleek blue suit. The result: a high-low look that we love.

Try It: Lean Into the Rock Star Aesthetic

Gary Clark Jr. wears a fedora while performing at the grand opening of The Theater
LAS VEGAS, NEVADA: Musician Gary Clark Jr. wears a fedora while performing at the grand opening of The Theater at Virgin Hotels Las Vegas on September 11, 2021. (Photo by Ethan Miller/Getty Images)

Even if you aren’t a Grammy-nominated, multi-platinum frontman with a garage full of six-figure cars, you can embody the effortless cool aesthetic of a rockstar. And it starts with a great hat. 

We love how guitarist Gary Clark, Jr. (seen above performing in Las Vegas) smartly curated his whole fit around his not quite cowboy Stetson style semi Western men’s fedora.

Start, like he did, with a wool or felt fedora and add in tight denim, slim suiting, and a leather jacket if the mood strikes you.

Add a dark pair of “I was up partying all night” sunglasses under your hat to fully complete the vibe.

Try It: Go Bright

Franklin Myrtle (R) wears a white hat while attending Sienna Li
NEW YORK, NEW YORK: Franklin Myrtle (R) wears a white hat while attending Sienna Li during NYFW: The Shows on September 12, 2021. (Photo by Paul Morigi/Getty Images)

When in doubt, go bright.

The power of a bright, white pork pie hat is unmatched especially, as stylist and model Franklin Myrtle demonstrates, when paired with an equally bright suit and black shirt.

Pictured here at NYFW, Myrtle glows in his wide brimmed white fedora and sleekly tailored suiting. 

The Hat Stops Here

Felt hats aren’t just accessories. They’re tokens of confidence. Truly great wool hats transcend dress codes, social status, and time. Men’s felt hats are stylish beacons telegraphing to the world that, yes, you care about how you look and, yes, no one is doing fashion better than you are right now. 

Wear a great hat, and you’ll instantly look like you have it all figured out. 

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