Why Don’t You … Wear a Little Ladylike Hat Like Jackie O

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In her famous column for Harper’s Bazaar, legendary editor Diana Vreeland issued our readers many dares: Why don’t you rinse your blond child’s hair in dead champagne to keep it gold? Why don’t you have every room done up in every color green? Why don’t you order Schiaparelli’s cellophane belt with your name and telephone number on it? In a new series, we’ll pose our own modern-day dares.

Why don’t you wear a chic little hat? That’s the question Joseph Altuzarra posed this Sunday at New York Fashion Week. This season, for his brand’s 15th anniversary, the designer created a nostalgic atmosphere, inviting close friends of the label to view his Fall 2024 collection in an intimate, salonlike setting at his showroom. The looks, too, interpreted elements from the past in a new, fresh way. Think: art deco meets all-American horse girls. Sleek styling featured fitted knit jodhpur-inspired pants, ankle-skimming dresses, and oversize coats with playful clownish ruffled collars—and atop it all was a modern take on the pillbox hat. In shades of black and white, these hats framed the brow—and put the perfect finishing touch on Altuzarra’s ladylike wardrobe.

If a pillbox hat sounds old-fashioned, and not in a good way, that’s part of the allure. As noted hat wearer, cult-favorite newsletter scribe, and Washington Post fashion writer Rachel Tashjian explains, “the fact that these more structured hats feel vintage is part of the appeal. It takes confidence to wear something that’s considered outdated.”

These accessories recall a time when there was more formality around getting dressed. “I also love the entire theater of ‘dressing,’ especially lately,” Tashjian adds. “I like the drama and ritual of creating an ensemble and topping it off with the right headgear, like a wax seal on a letter.” If you’re not yet sold, she has one final pitch: practicality. “If you have a bad hair day, you put on a hat and it looks like you spent 20 more minutes getting dressed,” she says.

Jalil Johnson, Saks fashion office coordinator and style star, was thinking about hats pre–Fashion Week. “Does anyone still wear a hat?” he wondered in an Instagram post, referencing a favorite Stephen Sondheim song, “Ladies Who Lunch,” and wearing a structured Gigi Burris cap. The answer: a resounding yes. So for Fashion Week, he wore a raffia hat from Jenny Walton.

“What I love about it is how whimsical and retro it is,” he says. Pairing the cap with a workwear jacket, button-up blouse, pencil skirt, slingback heels, and a Zankov x S.Joon mohair clutch, Johnson channeled the Prada Spring 2024 collection. “Although the show didn’t feature hats—the models actually wore jersey headbands—I thought the hat added an extra oomph.” Indeed. For a guiding mantra, Johnson suggests asking yourself WWJD—“What would Jackie do?” (As in, Kennedy Onassis.)

Laura Reilly, a fashion writer and founder of newsletter Magasin, is known for her well-documented Fashion Week looks. This season, she kicked things off in an ivory driver-style hat from the Row’s Spring 2024 collection. After seeing it in the brand’s look book and on Greta Lee at the 2023 SCAD Savannah Film Festival, Reilly polled her Substack followers about whether she should buy the hat. “Many of them said no lol,” she says. (She obviously did not listen.)

Fortunately, the reception was different IRL, thanks at least in part to Reilly’s masterful styling: Pairing the cream-colored hat with a belted, oversize gray coat, structured straw bag, and black Mary Jane flats proved a winning combination. Even if it wasn’t always the plan. “I had put [the look] together when planning out rough drafts of my outfits for the week—this was well before I even knew when the hat would be for sale,” she says. “When I finally had the hat in hand, I wasn’t sure I’d add it until I tried it on the morning of. I don’t think I could have pulled together a more hat-worthy look in the end, though.”

If you can’t wait until Altuzarra’s collection hits stores in the fall, Reilly suggests scouring the secondhand market, especially if you’re willing to deal with some trial and error. “I’ve been doing a lot of eBaying/Etsying felted hats lately, and the challenge I’ve come up against is that you can’t tell how exactly they’re going to sit on your crown,” she sats. “The best luck I’ve had is with hats with a slightly deeper dome, so that way, at least your head isn’t hitting the top of the hat while the brim flares awkwardly away, not quite sitting flat.”

So, why don’t you … start searching?

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