Amidst Copenhagen Fashion Week’s fall 2026 season, one thing was abundantly clear on the streets of the Danish capital: pillbox hats were overwhelmingly in. The retro look took on many forms, with guests donning neutral, leopard print, and embellished caps alike.
Recently, accessories have taken on a ’60s flavor amongst the celebrity and street style set. Jennifer Lawrence wore a leopard print hat with geometric cat-eye glasses and an oversized olive trench coat while out for a walk with her son, while Ayo Edebiri coordinated her black hat with a ladylike skirt suit at Chanel’s métiers d’art show in New York. Dakota Johnson and Kylie Jenner have also both rocked headscarves this winter.
The 1960s flair goes well beyond the headwear. Take a look at the 2026 awards season red carpets: Teyana Taylor accessorized with black leather gloves at the Critics Choice Awards, and Parker Posey and Odessa A’zion followed suit at the Golden Globes.
There is perhaps no bigger proponent of the ’60s look than Pamela Anderson, who embraced mid-century pieces—sometimes two at a time—throughout her Naked Gun press tour. On one outing, Anderson accessorized a floral Marni set with a ladylike white headscarf. Another appearance leaned more streamlined: a sleek black dress with a draped open back was styled with a leopard-print Gigi Burris pillbox. Rounding out the trio was a custom navy satin gown by Thom Browne, featuring a bateau neckline, floor-length A-line silhouette, and black mesh wrist-length gloves, accented with a custom diamond Pandora brooch.
The current penchant for retro accessories isn’t merely about nostalgia, but about giving modern looks an added touch of character. In the pre-fall 2026, Chloé showed pillbox hats worn with ’80s power shoulders and bubble peplums, while beaded tassel brooches dotted Dior, and Balenciaga styled full-length gloves with sports bras and hoodies. It was a continuation of spring 2026, where Chanel featured floral pins of all sizes and Prada paired with candy-colored statement gloves with house dresses.
But how did these accessories gain traction in the early ’60s to begin with? The short answer: Jackie Kennedy. Though her husband, President John F. Kennedy, favored forward-looking policies, the first lady’s fashion reflected classic, traditional femininity. Jackie’s ladylike style–including pillbox hats, brooches, gloves, and headscarves–quickly influenced the country’s idea of elegance and progress, one that was aspirational to women watching her on television. So while the average woman couldn’t exactly get her hands on Chanel couture, she could channel the first lady through her styling.
Many used accessories as a shortcut to getting Kennedy’s polished, new-Americana aesthetic. Investing in the finishing pieces instantly elevated a department-store look. “Women in the early 1960s often owned fewer suits or dresses, relying instead on accessories to refresh and vary their wardrobes,” explains Elizabeth L. Block, author of Gilded Age Fashion. “A well-made suit or day dress could be reworn again, with hats, gloves, brooches, jewelry, or a different blouse. Especially in winter, this approach was very practical.”
For Jalil Johnson, writer of the Substack Consider Yourself Cultured, the ’60s resurgence isn’t just an aesthetic choice—it also reflects certain similarities in the atmospheres of then and now. “JFK and Jackie Kennedy represented a breath of fresh air in the United States,” he points out, and New Yorkers in 2026 are experiencing something akin to that. “Just look at the mayor and the first lady of New York—they’re a young couple, bringing a new life into the city, and it feels like there’s new energy, new possibility,” Johnson says.
He also draws a parallel between the technological optimism in the ’60s and today’s conversations around AI. “If you think about it, there is a sense that we’re having our own kind of Space Race,” he says. “Maybe not in the same capacity as going to the moon, but in how fast things are advancing.”
Yet Johnson, paraphrasing Tom Ford, notes that every revival is shaped by its own time; even when the same accessories reappear, they’re filtered through today’s lens. For Patricia Voto, founder of ONE/OF, an upcycled label that uses reclaimed and vintage materials, making retro accessories feel modern comes down to creating a sense of contrast. “It’s okay to honor those time periods [by staying] true to the original proportions or shapes, but you’ve got to add some sort of unexpected twist to it, so it doesn’t feel like you’re wearing a costume,” she says.
Stylist Bailey Moon, who dressed Anderson throughout the Naked Gun press tour, says the appeal of the trend lies in the modern reinterpretation of these pieces. “For Pamela’s wrist gloves, we used a netted material, which felt like a new way of reworking a very classic trope,” Moon explains. “It makes it feel cool and modern, while still honoring the referential nature of it.” That same approach extended to headwear. “What’s exciting right now is how these accessories are being done in bolder ways—kerchiefs in red or jewel tones, or pillbox hats that aren’t traditional at all,” he adds. “Instead of a classic pillbox, it’s leopard, stripes, or something unexpected that gives the look a bit of counterbalance.”
And then there’s the question of attitude. “The biggest element for any consumer or person participating in this trend is you just have to own it,” Moon observes. Ultimately, the modern appeal of these accessories has less to do with following old codes than with confidently taking archival styles into the future.