Fall/Winter 2025 Is the Season of the Hat

Aside from a straw bucket hat at the beach or a knit beanie in winter, I’ve never really been a hat girl. Wearing one for fashion rather than function always felt a little extra for my introvert personality type. This season, though, something shifted. On the Fall/Winter 2025 runways, chic little vintage-inspired hats had presence without pretense: Jackie O pillboxes at Emilia Wickstead and Markarian, flapper-esque cloches at Miu Miu and Brunello Cucinelli, sculptural berets at Dior and Altuzarra, silk chiffon–trimmed boaters and felted sailor hats at Chanel and Loro Piana. I was surprised to find myself wanting to try a topper and wondering if I could actually pull it off.

When I mentioned my hesitation to milliner Gigi Burris, she invited me to her Chinatown studio during New York Fashion Week to play dress-up. Burris’s philosophy is to “dress from hat to toe,” favoring unexpected contrasts like a prim pillbox paired with a leather moto and jeans. But with just thirty minutes before my next show, we worked in reverse. Taking in my menswear-inspired tailoring, she lifted a ladylike halo of alabaster velour called the Laura from its stand and placed it gently atop my head. The modified pillbox with straight sides that subtly sweep into a wide cuff felt light as air, giving my look an effortless lift. In the mirror, I saw a more polished version of myself. “It’s very flattering because it draws the eye up,” Burris explained.

She’s not the only designer turning her gaze skyward this fall. Markarian’s Alexandra O’Neill looked to Tudor grandeur, collaborating with Burris to remix rich jewel-tone brocades from the 1500s with sleek accessories from the 1950s. “The Markarian woman wants to leave the house feeling fully dressed and considered, and punctuating her look with a pillbox hat achieves that,” O’Neill notes. Emilia Wickstead, meanwhile, translated the refined elegance of Edith Head’s costume designs for Alfred Hitchcock’s 1963 masterpiece The Birds into skirt suits styled with custom Laura Cathcart Millinery hats in the same striking chartreuse shade. “That 1960s silhouette can only be completed with a pillbox hat,” Wickstead says. The higher the hat, the closer to grace, it seems.

Roopal Patel, senior vice president and fashion director of Saks Fifth Avenue and Neiman Marcus, notes that hats have become central to the season’s mood. “It’s all about head-to-toe dressing, and the hat is literally the topper,” she says. “There are so many options to choose from. Fuzzy textures, artisanal hand knits, sculpted leathers, trappers, and luxe velvets—there is a hat for everyone.” For Patel, hats are also a reflection of individuality. “Hats really are a signature of one’s style and personality. I think of my colleague Chloe King, director of fashion and lifestyle, who always adorns her looks with the chicest hats.”

Hats are evocative of happy times. They’re just like a little pill of optimism. 

The trend also extends beyond the runway. “With [search term] interest in fashion hat hitting a record high over the past few months, the hat is the new It bag,” says Sagal Mohammed, editorial and creative lead for Google Shopping, who also highlights the pillbox baseball hat as among fall’s most sought-after styles. Actress and comedian Chloe Fineman created one with a short brim she calls the Co-Pilot as part of her retro-inspired capsule collection for Mother. “I co-wrote the SNL sketch ‘Big Dumb Hat’ partly as a dig at myself,” Fineman says. “Hats are sort of like wigs to me in that they’re totally transformative! I have a baseball hat with a team I don’t pay attention to; a big sun hat for the farmer’s market or to hide whatever medspa work I’ve done; and now, of course, my Mother hat to feel like a whimsical French girl.”

When I stopped by legendary London milliner Stephen Jones’s Covent Garden atelier the following week, he reminded me that, at least in the United Kingdom, hats have never lost their appeal. “There are just more occasions to wear one here,” he says. “Weddings, for example, are daytime events. The ceremony might be at 10 or 11 o’clock in the morning, and you’ll want a coat and a hat because you’ll be sitting outside, and it’s probably raining.” Among his many striking creations: a metallic-flecked tweed trilby, and a pearl-and-net-veil-trimmed Century beret for the Dior runway.

Jones welcomes both hat aficionados and the newly hat-curious. His advice for adding a new hat to your daily wardrobe is simple: “Wear it at home before you wear it out, so you’ll get used to how it feels on your head.” For beginners, he suggests starting small. “The learner’s permit for hats is a beret,” Jones explains. “You can buy them at every price point, and style them however you want.” He also points to a classic felt fedora as another great starter hat—timeless, versatile, and easy to wear. “Sometimes people say they don’t have the confidence to wear a hat, but I think the hat can be the confidence for you, and you can just relax underneath it,” he adds with a smile.

The accessory feels particularly of the moment due to a larger cultural craving. “I think hats are evocative of happy times,” says Jones. “They’re just like a little pill of optimism.” For me, that became literal. Throughout Fashion Month, I kept returning to the Laura—my pillbox of optimism—the one piece that made me stand taller and carry myself with quiet confidence. Hats, I realized, aren’t just about grabbing attention; they’re about wearing joy.