I love a good headpiece. What can I say – maybe Chloe King put pressure on me?! Pillbox hats came back into trend last year, which thrilled me, because I bought two from Canned Ham Vintage here in Sarasota a few years ago. These hats feel feminine and nostalgic, yet somehow modern and cool. Today, I’m reflecting on where pillbox hats originated, how they should fit, my current favorite styles, and how I’m wearing my hats!
Where did pillbox hats originate?
Pillbox hats are small, structured, hairless hats with straight brims and a flat top – simple in shape, yet incredibly attractive. While their exact origins are debated, there are several leading theories. Some historians associate this silhouette with early military caps, while others attribute the modern fashion version to 1930s Hollywood – notably Adrian’s designs for Greta Garbo. Of course, this style became truly iconic in the early 1960s when Jacqueline Kennedy made the pillbox hat a signature part of her polished wardrobe. No matter which origin story you subscribe to, their eternal appeal cannot be denied.
How should pillbox hats fit?
When it comes to finding the right fit, I would say there is often a little trial and error with these pieces. Most styles only come in one size, and fit really is everything. You don’t want it so big that it overwhelms your head, but you also don’t want it so small that it looks awkwardly placed at the crown. Over the years I’ve ordered a lot that didn’t work out – either too big or too small – and unfortunately, there’s really no good way to adjust them.
cap space
There are a few different ways to put on a pillbox hat. Personally, I wear my outfits in two ways. One look I like is to push the hat forward a bit so it’s about 1-2 inches above my eyebrows and tilt it just touching one side – Kate Middleton gets this look perfectly. Alternatively, I would place my hat back and in the middle for a more classic feel. For this, I take styling cues from Jackie O. not actually Correct Way to wear a pillbox hat, but these are the two places I like the most.
keep 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 I need a little more stability, I’ll sew a small comb (or two) into the inside layer. Then I lightly backcomb a section of hair, apply a little hairspray, and secure the comb in place in that area. Easy Peas.
Where to find the perfect pillbox hat
Normally, I would say that pillbox hats can be quite hard to find, but since they are currently on trend, they are more readily available from different brands and retailers right now. Although you can certainly get a new product from sites like Moda Operandi and Anthropologie, I would argue that some of the best styles are still found at 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 a pleasant experience to browse the different brands and narrow down your favorites. I’m currently loving all the pillbox styles from Lele Sadoughi and Gigi Burris. I’m especially impressed by this leopard one, this pink option and this absolutely classic style.
Of course, you can’t go wrong with something that’s winter-ready, like this 1960s mink hat or this rich chocolate brown version. And if you’re a bride-to-be, I love this gorgeous option with this white pillbox hat and exaggerated veil.
spring and summer styles
While most pillbox hats have a naturally fall or winter feel due to their wool, cashmere, or fur construction, don’t overlook spring or summer options. It’s perfect for under $35, and I love this elevated knit version. Not only are these styles the perfect accessory to any warm-weather frock, but they’re also incredibly easy to pack for travel.
How to Style Pillbox Hats
Okay, now on to the really fun part – how to style a pillbox hat! Let’s look at some ways I think these pieces will look incredible in 2026.
see a leopard
Okay, first I have to focus on styling this fabulous leopard hat. For this, I would like to keep the overall vibe retro and feminine. For a night out in NYC, you could wear it with this red gown and throw a faux fur jacket over your shoulders. I would totally finish the look with a red lip and, just for a touch of drama, add this affordable brooch. If red isn’t your favourite, no worries. Leopard pairs beautifully with many colors. You can’t go wrong with this hat in pale pink, emerald green, or even baby blue.
a wedding ootd
Let’s pretend for a moment and dream of being a bride. I would absolutely love styling this pillbox birdcage hat for a winter courthouse wedding. Pair it with this dress, which is the perfect marriage 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, luxurious and can even become your “something blue.”
a classic look
As a lover of classic fashion, I can’t stop styling a timeless black pillbox hat. I often dream about this coat, and I think it would look so beautiful with one of these sophisticated styles. The beauty of this type of coat is that it can Happen Organization. I’d wear it with a sleek, simple pair of these satin olive pants and black flats. This bag will be the perfect finishing touch.
Resort-ready
Okay, switching gears completely, let’s talk resort wear. I’d love to style this knit pillbox hat, or this one, in a more whimsical, warm-weather way. Both would look perfect with this dress and these raffia slides I recently preordered. For this outfit, I would keep the bag summery but high, like this drawstring style I have my eye on. Talk about a great vacation look!
Final Thoughts on Pillbox Hats
It’s clear that I’m very excited about this current trend! I just love how cute, adorable, and timeless pillbox hats look – and all the fun ways to style them, too. Will you try these hats? 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 Build a Classic Fashion Wardrobe: Timeless Style Tips
Best jean shorts: top 5 pairs, test and reviews
Best Clothing Color Combination Guide
How to Find Your Style: Defining Your Personal Best Fashion
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