In 1961, Jackie Kennedy attended her husband John F. Kennedy’s inauguration, clad in a gorgeous beige Oleg Cassini coat. But the real pièce de résistance of her look was the coordinating egg-shaped Halston pillbox hat that sat atop her head. After the former first lady single-handedly popularized the look, other female figures like Audrey Hepburn and Princess Diana followed suit, co-signing the intriguing accent. Fast forward to today, and it almost feels like we’re back in the 20th century, at least sartorially speaking, as the pillbox hat has been resuscitated — and is perhaps more popular than ever.
Fashion historian Fiona Tedds finds it fascinating that the accessory is making a comeback in 2025, especially because pillbox hats haven’t been around for a while. “Designers are once again rehashing the past,” she explains. Tedds also believes the trend ties into the industry’s renewed interest in tailoring and women’s suiting. “The pillbox hat is a great shape to go with that sort of look.” And because other hat silhouettes have been done to death (bucket silhouettes, specifically), the fashion historian thinks this unconventional style is a fresh alternative to others on the market.
The hat’s bold energy is enticing to fashion girls as well. “What I love most about it is its minimal yet striking shape — clean, elegant, and endlessly chic,” explains Silvia Dusci, a content creator and founder of jewelry brand lesundial. “It has the unique ability to elevate even the simplest outfit, adding character without overpowering.” And the silhouette is universally flattering, too, according to Dusci. “It’s light, easy to wear, and leaves the face beautifully framed,” she says. “For me, it’s a perfect mix of timeless style and modern ease.”
Ahead, see how the fashion pack is styling their pillbox hats in 2025.
Cool & Casual
New York-based stylist and influencer Coco Schiffer is another pillbox hat connoisseur. “The second I put a pillbox hat on my head, I instantly feel more confident,” she tells TZR. “There’s something about the fact that no one really wears them, so they become a conversation starter.” The piece can make any outfit — even something as simple as a white tee and jeans combo — look more elevated, she adds.
A Little Quirky
You might as well wholeheartedly embrace the vintage-inspired trend with a quirky pillbox hat, such as this feather-adorned creation. To avoid the look coming off as costume-like, ground the accessory with classic neutral separates and sleek square-toe sandals.
A Case For Lace
Duschi enjoys styling her pillbox hat with clean, refined getups. “For summer, it’s all about playing with materials,” she explains. Here, the fashion insider juxtaposed her wool accent with flowy lace pants. Square-shaped sunglasses and chunky jewelry play up the warm-weather-ready vibes.
Suit Up
As Tedds mentioned, a pillbox hat pairs well with your menswear-inspired looks like, for example, a tie and button-up. In the summer, swap your blazer for a suiting vest. Finally, add some flair to the ensemble with pointy-toe boots and a slouchy bag.
Minimalism At Its Finest
When in doubt, go for an all-black outfit. With the addition of a fun, statement-making pillbox hat, the ensemble is anything but boring. Finish with a strappy sandal or loafers, depending on what the day calls for.
