I love a bold ensemble. One that shows confidence and personality by the bucket loads, standing out with bright colors and daring prints. Much to my delight, the latest looks are featuring both at the same time – topped with great hat styles for an extra dash of, well, extra.
After over a year of being confined to the shadows of our homes, we’re finally able to step out again and show off our personal style. Now, The Hatwalk is turning its analytical eye on the hottest men’s and women’s hat styles. We’re peeping the bowlers, boaters, fedoras and gambler hats being worn at recent A-list events, such as The Met Gala, runway shows, and film premieres. It’s become clear that I’m not the only one who wants to wear all my hats in a very big way right now.
In short, bland is absolutely banned.
In my opinion, the only shade that should be given to these style setters, is the one that’s cast from below the brim of their larger-than-life hats.
Who Wore It Where
If a hat trick is three consecutive successes then these famous faces have hit a style home run. Each one paid attention to silhouettes, textures, prints, or color schemes to bring a unique style to the red carpet.
Bright Brim Delight at the Met Gala

The first of three bold looks is a head-to-toe ocular oasis of chaotic prints and color combos. And it was worn by none other than Chef Marcus Samuelsson for the 2021 Met Gala in New York.
The theme of the night was “In America: A Lexicon of Fashion.” This look proved the Top Chef winner serves fashion looks as well as he does dishes in his celebrated New York City restaurant. In fact, he has likened getting dressed for the red carpet to preparing a new plate. And he clearly revels in coming up with interesting outfits.
But his looks didn’t hit equally for everyone.
His custom Dapper Dan Harlem suit, worn with a contrasting horizontal print waistcloth, rainbow cape, and two-toned felt hat ended up getting vastly different reviews. His hat, a red and white style reminiscent of a homburg hat, had a center dent running down the crown, or a gutter crown. But, unlike a traditional black or gray homburg hat, his featured a flattened brim without a pencil curl and modern color-blocking.
Stylecaster editors loved what he brought – and they previously dubbed him the honor of being of The 50 Most Stylish New Yorkers.
Meanwhile, Highsnobsociety put this look on the list of worst dressed Met Gala attendees. He said, “Why did Marcus Samuelsson show up to the Met Gala dressed like my sleep paralysis demon?”.
As for us? We love any hat ensemble that evokes such a polarizing view.
Bold freedom of expression is innately American. Add in loud, in-your-face prints that show off the wearer’s individuality and a nod to the LGBTQ+ community with a superhero-esque cape (what is a Marvel superhero if not American?!?) and we think Samuelsson’s Met Gala look is an on-theme hat trick.
Why It Works:
Samuelsson clearly understands that the key to mixing patterns is unifying them with a similar color palette and geometric prints with similar shapes. He expertly ties everything together with an overarching black and white color scheme.
He also kept busy prints away from his face, opting for a crisp white button up and black silk lapels on his suit. The red underside of the brim of his white wide brim felt hat draws your eye to his smile. It also sets the stage for bold punches of color in the patterned waistcloth and rainbow cape.
How to Wear It:
Like Samuelsson, start your look with a two-tone wide brim hat with two-tone edging and a reptilian-inspired hand band. Look for one with surprising details on the underside of the brim or a contrasting trim that encircles the entire hat. Extra points if you found a geometric or snakeskin-inspired hat band that is reminiscent of the pattern on Samuelsson’s Met Gala suit.
Then, choose a patterned ensemble with a color theme that matches the color of the trim. Polish it off by choosing shoes or heels that match the colors of your hat. This is a way of bookending your outfit with complementary pieces.
Black Bowler in Miami

The second look shows us that you don’t need a huge hat to make a big splash at this boho style event. Celebrity stylist and image consultant Wiwa Rivera attended Miami Fashion Week’s shows in a petite black bowler hat, a silk button-up shirt dress, and piled on accessories.
The busy silk pattern of her mini dress brings to mind Versace’s iconic baroque print. Meanwhile, her hat adds a dash of René Magritte surrealism for an outfit that is its own unique work of art.
Why It Works:
Though this look is loud, the elements that make it work well are more subtle. For us, it’s that the round silhouette of her bowler hat is complemented by other details in her outfit. You’ll notice round sunglasses, a round tote bag, and round organic shapes in the print of her dress. She also only used black accessories, keeping the focal point on her silk shirt dress.
We love to see a stylist at work, and applaud Rivera for her attention to every detail in a bold ensemble.
How to Wear It:
Flip Rivera’s look and go for a boldly printed hat with a neutral outfit – or wear a print from head-to-toe.
Any hat with a dramatic, all-over pattern is going to steal the show. We can already visualize a merlot and tan women’s boater hat matched with a matching silk button-up tucked into straight leg jeans with embroidered pocket details. Add a black oversized clutch to ensure you’ve got this hat trick in the bag.
And the other cool thing about the black derby is they are easily packable so if you’re popping down to Miami, they make a great travel hat.
A Pink Perfection in Paradise

A pink cowboy hat shouldn’t work with a dressed-up jumpsuit. Or on anyone over the age of five. In theory. But remember how we said we’re throwing away fashion rules?
Enter Malia Ward and her pale pink cowboy hat with a thin white band.
A premier for a surfing show may seem like an unexpected occasion to don a cowboy hat. But when you consider that both a sun-tanned surfer and trail-hardened cowboy are two iconic symbols of American culture, you’ll realize that Ward is on to something.
Looking effortlessly chic, she paired one of this year’s hottest hat styles with a well-tailored, navy blue and white pinstripe jumpsuit and coral heels. The vertical stripes of her outfit help to draw your eye up to her hat, which is perfectly poised on her tight curls.
Why It Works:
Malia didn’t hold back here. She chose to wear a bold pink cowboy hat with an even-bolder pinstripe jumpsuit. The squared-off shape of her cowboy hat and her form-fitting jumpsuit are both expertly tailored to show off her physique.
But notice there isn’t a big belt buckle or boots anywhere in sight? That’s how she kept this chic, not country.
How to Wear It:
Knowing how to wear a cowboy hat without going full country can be an art form. Luckily, we’re here to give you the cheat codes.
Let the cowboy hat be your own western-inspired outfit detail. Then, experiment with unexpected color combinations or textures. Pair a cream or light brown leather version of a western-inspired women’s fashion hat with a silk slip dress and strappy heels. Bring along an oversized blazer in the same color as your dress to complete the look for nighttime.
The Hat Stops Here
After a year of event cancellations and limited red carpet opportunities, Hollywood is stepping out in some of their boldest looks. And we see plenty of new hat styles that we love.
You’ll find zero yawns here. But disclaimer: these hat styles and patterned outfits are not for the faint of heart.
Every look is certainly not for everyone. One in particular has a very outspoken critic that held nothing back. But that’s exactly what makes these work that much more. Individuality is exalted. New silhouettes are celebrated. Fashion rules don’t exist.
In addition to curating the team of chefs for this year’s #MetGala, I’m also honored to attend wearing a custom suit designed by Harlem icon @DapperDanHarlem. This fashion legend burst onto the scene in the 80s by fusing high fashion & hip hop culture and created a lasting legacy pic.twitter.com/Wy9ByC5Sl1
— Marcus Samuelsson (@MarcusCooks) September 13, 2021
If you’re new to wearing patterns and hats, look to Wiwa Rivera’s style for inspiration. You’ll learn how to anchor a statement dress with neutral accessories and a black bowler hat. Excited about prints, but intimidated by mixing and matching different colors? Follow Marcus Samuelsson’s lead and jump into a busy print in black and white (sans the rainbow cape). And if you’re ready to embrace a bold hat and printed ensemble with abandon, use Malia Ward’s pink cowboy hat look as outfit inspiration.
The best thing about these bold hat styles is that they rely on personal taste over fleeting fads – because nailing bold style is all about owning your style. The only prerequisites a bold outfit requires are confidence and a strong desire to stand out. True, your own sartorial taste will evolve over the years. But it won’t be the fashion industry dictating what hat styles you need to be wearing at any given moment.
This is your permission slip to ban bland outfits once and for all.