<p>Cynthia Erivo isn't the only celebrity to embrace the Jackie Kennedy-reminiscent style lately. We break down the trend and top shopping options.</p>

<p><span style="font-weight: 400;">Although the history of the pillbox hat goes back to Roman times when soldiers wore them as military headgear, this small, round hat gained its widespread popularity in the 1930s before it hit its peak in the 1950s and 1960s. With First Lady <a href="https://www.lofficielusa.com/pop-culture/jfk-jacqueline-kennedy-troubled-love-life-relationship-marriage" target="_blank" rel="noopener">Jacqueline Kennedy</a> wearing a cream pillbox hat to her husband&rsquo;s inauguration at the White House and style icons of the time like <a href="https://www.lofficielusa.com/fashion/audrey-hepburn-givenchy-little-black-dress-history" target="_blank" rel="noopener">Audrey Hepburn</a> and <a href="https://www.lofficielusa.com/fashion/princess-diana-john-travolta-dress-white-house-1985" target="_blank" rel="noopener">Princess Diana of Wales</a> embracing the look soon after, it was no surprise that this flat-topped hat became the ultimate symbol of understated elegance of that period.&nbsp;</span></p>
<p><span style="font-weight: 400;">While <a href="https://www.lofficielusa.com/beauty/jackie-kennedy-10-lessons-style-beauty" target="_blank" rel="noopener">Jacqueline Kennedy</a> is the indisputable icon of the pillbox look, <em><a href="https://www.lofficielusa.com/fashion/cynthia-ervio-ariana-grande-best-witchy-looks-wicked-press-tour" target="_blank" rel="noopener">Wicked</a></em>&rsquo;s buzzy 2024 press tour placed <a href="https://www.lofficielusa.com/film-tv/cynthia-erivo-films-tv-iconic-roles-wicked-broadway" target="_blank" rel="noopener">Cynthia Erivo</a> as a modern contender for the ambassador of this hat style. With mouth-dropping <a href="https://www.lofficielusa.com/fashion/thom-browne-wicked-gowns-ariana-grande-cynthia-erivo-the-met-atelier-alina-cho" target="_blank" rel="noopener">Thom Browne</a> looks styled alongside her contemporary iterations of the pillbox hat, we all </span><span style="font-weight: 400;">held space</span><span style="font-weight: 400;"> for the actor&rsquo;s unexpected masterclass in headpieces and fascinators.&nbsp;</span></p>
<p><span style="font-weight: 400;">Looking at the bigger picture, it's clear that pillbox hats have been begging for their comeback since the <a href="https://www.lofficielusa.com/beauty/spring-summer-2025-runway-hair-trends" target="_blank" rel="noopener">Spring/Summer 2025 runways</a>&mdash;and even the <a href="https://www.lofficielusa.com/fashion/fall-winter-2024-fashion-trends-runway" target="_blank" rel="noopener">Fall/Winter 2024</a> shows. Brands like <a href="https://www.lofficielusa.com/fashion-week/chloe-spring-summer-2025-pfw-paris-fashion-week-runway-looks" target="_blank" rel="noopener">Chlo&eacute;</a> and <a href="https://www.lofficielusa.com/fashion-week/valentino-haute-couture-spring-summer-2025-alessandro-michele" target="_blank" rel="noopener">Valentino</a> showcased a stylish display of flat-topped headpieces in multiple colorways and textures. Far from embodying the classic '60s elegance, these modern pillbox hats were paired with bold, maximalist looks, speaking to a new type of cool-girl.&nbsp;</span></p>
<h2 style="text-align: center;"><strong>Pillbox Hats on the Runway</strong></h2>

Chloé Spring/Summer 2025. Getty Images.

Loro Piana Spring/Summer 2025. Loro Piana.

Maria McManus Spring/Summer 2025. Maria McManus.

Valentino Spring/Summer 2025. Getty Images.

<p><span style="font-weight: 400;">While pillbox hats stand out for their simplicity and elegance, this brimless accessory is more versatile than it seems. Depending on the shape and size of the hat, this circular style can be worn pinned to the hair or placed at different angles to achieve many distinct looks. Plus, these small hats have a slighly different character depending on their details, like if they're embellished with lace, veils, feathers, brooches, or any other desired adornments for a more striking look. Whether crafted in velvet, satin, wool, or silk, pillbox hats symbolized sophistication and timeless charm for decades.</span></p>
<h2 style="text-align: center;"><strong>Jacqueline Kennedy Onassis and Princess Diana Wearing Pillbox Hats</strong></h2>

Jacqueline Kennedy Onassis. Getty Images.

Diana, Princess of Wales. Getty Images.

<p><span style="font-weight: 400;">While houses like <a href="https://www.lofficielusa.com/fashion/loro-piana-history-brand" target="_blank" rel="noopener">Loro Piana</a>, Maria McManus, and <a href="https://www.lofficielusa.com/fashion-week/altuzarra-fall-winter-2024-nyfw-show-runway-images" target="_blank" rel="noopener">Altuzarra</a> offered a more minimalist take on the pillbox style, they also proved that this charming hat silhouette can be seamlessly incorporated into urban attire. Paired with pleated skirts and casual sandals, these modern iterations of the classic pillbox look have the potential to become one of the must-have accessories of 2025.&nbsp;</span></p>
<p><span style="font-weight: 400;">From renowned h<span>eadwear </span>names like Gigi Burris and Esenshel to contemporary fashion labels like Toteme and Nana Jacqueline, keep scrolling to shop </span><i><span style="font-weight: 400;">L&rsquo;OFFICIEL</span></i><span style="font-weight: 400;">'s favorite pillbox hats (and some other headpieces that capture the same vibe).</span></p>

<p>In silk and denim iterations, Loro Piana's take on pillbox hats is one for the minimalistic modern woman. <span>Honoring the beloved First Lady, the luxurious feel and immaculate appearance of the Jacqueline hat reflects the eternal grace of Loro Piana.</span></p>
<p><em>Loro Piana Jacqueline Hat Silk Viscose, $1,450, <a href="https://us.loropiana.com/en/woman/accessories/hats/jacqueline-hat-FAO7106_W000_M.html?gad_source=1&amp;gclid=Cj0KCQiAwOe8BhCCARIsAGKeD56Oahvf2QDnPYm6lpnZESzlwjIgT3UNPBxR2qMIB31yNcvFX6QbYuEaAkb8EALw_wcB&amp;gclsrc=aw.ds" target="_blank" rel="noopener">Loro Piana</a></em></p>

Loro Piana Pillbox Hat

Loro Piana

<p>100% handmade in sturdy fur felt, Mains De Vapeur's tall take on the classic pillbox hat can seamlessly adapt to any urban wardrobe. Crafted in <span>their New York studio, this charming design comes in white, teal, and brown iterations, offering versatility for various wear occasions.</span></p>
<p><em>Mains De Vapeur Pillbox, $395, <a href="https://mainsdevapeur.com/collections/pillbox/products/pillbox-1" target="_blank" rel="noopener">Mains De Vapeur</a></em></p>

Mains De Vapeul Pillbox

Mains De Vapeur

<p>Toteme's cold-weather-approved take on pillbox hats is one to keep you warm all winter long. C<span>rafted from cozy shearling with a soft shaved finish, this chic design can be paired with anything from casual jeans to more elegant wintertime attire. For a fuzzier look, explore its butter and navy iterations.</span></p>
<p><em>Toteme Shearling Pillbox Hat Bark, $285, <a href="https://toteme.com/products/shearling-pillbox-hat-bark" target="_blank" rel="noopener">Toteme</a></em></p>

Toteme Pillbox Hat

Toteme

<p>An expert in anything millinery, Gigi Buris offers and array of c<span>arefully handmade hats for the bolder dressers. Available in seven different colorways, Gigi's modern take on the pillbox hat features a wide cuffed cap and is designed to sit towards the back of the head.</span></p>
<p><em>Gigi Burris Laura Dusty Rose, $385, <a href="https://gigiburris.com/products/laura-dusty-rose?variant=40657267032134" target="_blank" rel="noopener">Gigi Burris</a></em></p>

Gigi Burris Pillbox Hat

Gigi Burris

<p><span>Embracing beauty and femininity, Nana Jacqueline offers a collection of 60s-inspired suits and sets for those who adore a retro look. The Keira Diamond Hat serves as the perfect finishing touch to their matching satin skirt-and-top ensemble. Featuring elegant pleats and a sparkling embellishment, this flat-topped hat comes in four different colorways.</span></p>
<p><em>Nana Jacqueline Keira Diamond Hat, $110, <a href="https://nanajacqueline.com/products/keira-hat-pink-cream" target="_blank" rel="noopener">Nana Jacqueline</a></em></p>

Nana Jacqueline Pillbox Hat

Nana Jacqueline

<p>Featuring a turban-inspired design, this rigid headpiece by Valentino is one to adapt to any aesthetic. Whether you are a maximalist, a coquette lover, or a fan of quiet luxury, this bohemian twist on the pillbox hat is sure to bring out the cool girl inside of you.</p>
<p><em>Valentino Rigid Wool-Blend Turban, $1,690, <a href="https://www.neimanmarcus.com/p/valentino-rigid-wool-blend-turban-prod275520360?pimId=401248526787&amp;utm_source=google_shopping&amp;ecid=NMCS_GP_NC&amp;gad_source=1&amp;gclid=Cj0KCQiA4-y8BhC3ARIsAHmjC_GK_VtqtXRR1S_D68ISROpybPxSlt7Jw9S0hJ38ZmMtryWNtkLX5QcaAoE_EALw_wcB&amp;gclsrc=aw.ds" target="_blank" rel="noopener">Neiman Marcus</a></em></p>

Valentino Pillbox Hat

Valentino

<p>From structured beanies to towering straw hats, Anthony Peto adds a unique, quirky twist to headwear. His <span>military-inspired Calot Mohair hat is crafted from gentle, luxurious fabrics and features a feminine palette that captures the essence of winter.</span></p>
<p><em>Anthony Peto Calot Mohair, $167, <a href="https://anthonypeto.com/collections/women/products/calot-mohair" target="_blank" rel="noopener">Anthony Peto</a></em></p>

Anthony Peto Pillbox Hat

Anthony Peto

<p>Did Cynthia Erivo looks inspire you to expand your hat collection? Then look no further than Esenchel. Known for its unique takes on contemporary headwear featuring exaggerated proportions in eye-catching palettes, no one can craft a modern pillbox hat quite like Esenchel.</p>
<p><em>Esenchel W24 Cushion Beret Hat, $455, <a href="https://esenshel.com/products/w24-cushion-beret-hat" target="_blank" rel="noopener">Esenchel</a></em></p>

Esenchel Pillbox Hat

Esenshel

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<p><span>L'OFFICIEL USA&nbsp;</span><i><span>may be compensated and/or receive an affiliate commission if products are purchased through our links. This item was gifted. Neither decide our editorial decisions.</span></i></p>
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Are We Dressing Like First Ladies Now? A Pillbox Hat Trend Explainer

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