The Best Fall 2023 Hats to Wear This Season

When you think of summer hats, rattan wide-brims and canvas bucket hats likely come easily to mind. But what about the toppers intended for the colder seasons? Does your imagination stop at the basic beanie? Trend forecaster Jessica Richards implores you to expand your perspective, especially since fall hats, in particular, have the potential to be the hardest-working element of your outfit. Allow Richards to elaborate: "Hats are the extra bit of decoration we'll see this fall season as part of an ethos of completely showy and over-the-top dressing. We're experiencing a continued sentiment towards 'more is more'—and then on top of that, add a hat, too!"

As for how the fashion analyst came to her conclusion that maximalism is influencing fall 2023's hat trends, she observed the fashion crowd in its wild and natural habitat: Strutting the streets during fashion month. "Street style has always been about attention to detail to the 'full look,' but we're seeing more than ever that hats are often playful additions to already striking styling," Richards details over email. "And throughout fashion month, the global street style we saw in every city reinforced that this bold accessorizing trend is incredibly important. Bright and fuzzy bucket hats for Prada (but not from the brand!) and loads of sporty chic Gucci x Adidas silhouettes in Milan, for example."

Ahead, Richards elaborates on her findings and shouts out the specific women's fall hat silhouettes you should consider snagging. Ranging from cool-girl baseball caps to French-inspired fashion berets, if you weren't hat person before, well, you certainly are now.

Fuzzy Bucket Hats

Richards notes that fall 2022 will see "the continuation of the oversized, overdyed, and colorful furry bucket hat." You've absolutely seen the silhouettes on a crop of A-listers, most notably the one, the only Rihanna, who wears them for a gamut of occasions, including date nights with partner A$AP Rocky. The Savage x Fenty founder, along with Emily Ratajkowski, Dua Lipa, and Bella Hadid, has a particular penchant for the plush buckets made by Kent-based milliner Emma Brewin. 

To wit, Brewin believes that her viral fuzzy bucket hats are much more than a statement throw-on. "For me, they are so much more than an accessory," she says over email." One of my customers once described theirs as their emotional support animal, and I feel that." Furry bucket hats are comfort dressing in its most glamorous, "Who me? Oh, I just got back from the ski lounge in Aspen" manifestation. 

Baseball Hats

"Vintage-inspired, classic baseball caps are the perfect accessory to top off your fall look for a completely laidback feel," details Jenna Woodhull, Vice President of Design and Product at California-based hat brand Brixton. "Baseball hats have a way of making any outfit look completely effortless." As for styling the sporty staple, Richards advises you to opt for the unexpected route. Instead of an athletic ensemble, try "[contrasting] chic baseball caps against oversized tailoring"—as seen above on the incomparable fashion influencer and All The Pretty Birds founder, Tamu Mcpherson.

Berets

"I'd also predict that with this bit of momentum in preppy dressing, we'll see a beret moment, with some combined with a net veil detail to balance sophistication with drama," says Richards. But if you're not drawn to beret styles that exude a widow-at-her-fifth-husband's-funeral type of vibe, opt out of those with mesh overlays and try a classic silhouette in knit or felted fabrications. As for how to wear a beret, lean into its Parisian-prepster roots by wearing front-pleat trousers, a Breton-striped sweater, and ballet flats.

Newsboy Hat

"On the more chic side, both preppy and tailored uniform-inspired dressing à la Dior and The Frankie Shop, amongst others, encourage more streamlined hat silhouettes like pageboy caps (also known as newsboy hats)," Richards offers. And when it comes to shopping the style, you can't do better than Brixton, as the headwear label's become almost synonymous with the flat silhouette. 

"The Brixton Hooligan or Brood Newsboy Cap were the first items the brand ever made, so we love seeing these styles back in the limelight," details the brand's Vice President of Design and Product. And, while they're peaking in popularity this fall, they are and always will be in style. "The timeless look of these means they’ll always have a place in your wardrobe, too," Woodhull points out.

Western Hats

Richards says fall 2022 will also be the season of the cool-girl cowgirl. "From both designer and vintage markets, the Western hat trend continues as well; What better styling to encourage oversized and very present styling? Bigger is better and so is drama this season when it comes to hats." Giddy up this season in wide-brim hats in unexpected, feminine colors and textiles like tweed or ultra-soft felt.

Meet the Experts

Jessica Richards

Jessica Richards is a trend forecaster, style storyteller, and founder of JMR Trend + Creative, whose synergistic focus inspires what is now and next. With an extensive background in forecasting, concepts, and design for major North American retailers, she brings a forward-thinking yet commercially and brand-right viability to projects across the fashion and wellness

industries.

Emma Brewin

Emma launched her eponymous label in 2014 and has always had a clear vision to make pieces that last a lifetime in both quality and design.  

Every piece is designed and handmade, from start to finish, in the brand's Kent-based studio by Emma and her small team. Traditional techniques and processes are used to ensure every hat is made to the highest quality possible.

Jenna Woodhull

Jenna Woodhull is the VP of Design and Product at Brixton, where she joined the company in 2012.  She oversees product creation including design and development for the Southern California-inspired apparel and headwear brand. Prior to joining the Brixton team, she served as Volcom’s VP of Product working directly with French luxury group Kering. She has also worked as the VP of Womens Product at Nike/Hurley.