I love a good headpiece. What can I say – maybe Chloe King has rubbed off on me?! Pillbox hats started trending again last year, which absolutely thrilled me, since I had picked up two at Canned Ham Vintage here in Sarasota a few years back. These hats feel feminine and nostalgic, yet somehow still modern and cool. Today, I’m diving into where pillbox hats originated, how they should fit, my current favorite styles, and how I’m wearing mine!
Where Did Pillbox Hats Originate?
Pillbox hats are small, structured, brimless hats with straight sides and a flat top – simple in shape, yet incredibly chic. While their exact origins are debated, there are several leading theories. Some historians trace the silhouette back to early military caps, while others credit the modern fashion version to 1930s Hollywood – particularly Adrian’s designs for Greta Garbo. Of course, the style became truly iconic in the early 1960s when Jacqueline Kennedy made pillbox hats a signature part of her polished wardrobe. No matter which origin story you subscribe to, there’s no denying their timeless appeal.
How Should Pillbox Hats Fit?
When it comes to finding the perfect fit, I’ll say it often takes a bit of trial and error with these pieces. Most styles come in just one size, and the fit truly is everything. You don’t want it so large that it overwhelms your head, but you also don’t want it so small that it looks awkwardly perched on the crown. I’ve ordered plenty over the years that simply haven’t worked – either too big or too small – and unfortunately, there really isn’t a good way to adjust them.
Hat Placement
There are a few different ways to position a pillbox hat. Personally, I tend to wear mine two ways. One look I love is pushing the hat slightly forward so it rests about 1–2 inches above my eyebrows and tilting it just a touch to one side – Kate Middleton achieves this look perfectly. Alternatively, I’ll position my hat farther back and centered for a more classic feel. For that, I take styling cues from Jackie O. There’s truly no right way to wear a pillbox hat, but these are the two placements I prefer most.
Keeping Your Hat in Place
Once you’ve decided how you want to wear your hat, you’ll want to make sure it’s secure. If mine needs a bit more stability, I’ll stitch a small comb (or two) into the inside lining. Then I lightly backcomb a section of hair, add a bit of hairspray, and secure the comb into that area. Easy peasy.
Where to Find the Perfect Pillbox Hat
Generally, I’d say pillbox hats can be quite hard to find, but since they’re currently trending, they’re more readily available from a variety of brands and retailers right now. While you can certainly scoop up a new one from sites like Moda Operandi and Anthropologie, I’d argue that some of the best styles are still found in local vintage and thrift stores, as well as from artisans on Etsy.
My Current Favorite Pillbox Hats
With so many new styles being released, it was such a treat to browse through different brands and narrow down my favorites. I’m currently loving all the pillbox styles from Lele Sadoughi and Gigi Burris. I’m especially smitten with this leopard one, this pink option, and this perfectly classic style.
Of course, you can’t go wrong with something that feels winter-ready, like this 1960s mink hat or this rich chocolate brown version. And if you’re a bride-to-be, I adore this white pillbox hat and this gorgeous option with an exaggerated veil.
Spring & Summer Styles
While most pillbox hats feel inherently fall or winter due to their wool, cashmere, or fur fabrications, don’t overlook a spring or summer option. This one is perfect at under $35, and I absolutely love this elevated woven version. Not only are these styles the perfect accessory for any warm-weather frock, but they’re also incredibly easy to pack for travel.
How to Style Pillbox Hats
Okay, now onto the really fun part—how to style pillbox hats! Let’s dive into a few ways I think these pieces will look incredible in 2026.
A Leopard Look
Okay, first I have to take a stab at styling this fab leopard hat. For this one, I’d want to keep the overall vibe feeling retro and feminine. For a night out in NYC, you could pair it with this red gown and drape a faux fur jacket over your shoulders. I’d absolutely finish the look with a red lip and, for just a touch of drama, add this affordable brooch. If red isn’t your thing, no worries. Leopard pairs beautifully with so many hues. You can’t go wrong with light pink, emerald green, or even baby blue alongside this hat.
A Wedding OOTD
Let’s play pretend for a moment and dream about being a bride. I would absolutely love to style this pillbox birdcage hat for a winter courthouse wedding. Pair it with this dress, which is the perfect marriage (pun intended) of a fun frock and a tailored blazer moment for the court. To complete the look, you can’t go wrong with these crystal-embellished flats. They’re comfortable, stunning, and could even serve as your “something blue.”
A Classic Look
As a lover of classic fashion, I couldn’t skip styling a timeless black pillbox hat. I often dream about this coat, and I think it would look so elegant paired with one of these refined styles. The beauty of a coat like this is that it can be the outfit. I’d wear it with these satin olive pants and a chic, simple pair of black flats. This bag would be the perfect finishing touch.
Resort-Ready
Okay, completely switching gears, let’s talk resort wear. I’d love to style this woven pillbox hat, or this one, in a more whimsical, warm-weather way. Both would look perfect paired with this dress I recently preordered and these raffia slides. For this outfit, I’d keep the bag summery yet elevated, like this drawstring style I’ve been eyeing. Talk about a great vacay look!
Final Thoughts on Pillbox Hats
It’s clear I’m very excited about this current trend! I just love how elegant, chic, and timeless pillbox hats feel – and all of the fun ways to style them. Will you be giving these hats a try? If so, I hope these styling tips and outfit ideas inspire you to experiment with them this season.
For more fashion inspiration, be sure to check out these posts:
How to Create a Classic Fashion Wardrobe: Timeless Style Tips
Best Jean Shorts: Top 5 Pairs, Tested & Reviewed
The Ultimate Clothing Color Combination Guide
How to Find Your Style: Defining Your Personal Best Fashion
The post How to Wear Pillbox Hats: The Ultimate Styling Guide appeared first on Atlantic-Pacific.
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