I really like a great headpiece. What can I say – possibly Chloe King has rubbed off on me?! Pillbox hats began trending once more final yr, which completely thrilled me, since I had picked up two at Canned Ham Vintage right here in Sarasota just a few years again. These hats really feel female and nostalgic, but someway nonetheless fashionable and funky. Right now, I’m diving into the place pillbox hats originated, how they need to match, my present favourite types, and the way I’m sporting mine!
The place Did Pillbox Hats Originate?
Pillbox hats are small, structured, brimless hats with straight sides and a flat prime – easy in form, but extremely stylish. Whereas their precise origins are debated, there are a number of main theories. Some historians hint the silhouette again to early army caps, whereas others credit score the fashionable style model to Nineteen Thirties Hollywood – significantly Adrian’s designs for Greta Garbo. After all, the fashion grew to become really iconic within the early Nineteen Sixties when Jacqueline Kennedy made pillbox hats a signature a part of her polished wardrobe. Regardless of which origin story you subscribe to, there’s no denying their timeless appeal.
How Ought to Pillbox Hats Match?
In relation to discovering the proper match, I’ll say it typically takes a little bit of trial and error with these items. Most types are available in only one dimension, and the match really is all the things. You don’t need it so massive that it overwhelms your head, however you additionally don’t need it so small that it appears to be like awkwardly perched on the crown. I’ve ordered loads over time that merely haven’t labored – both too huge or too small – and sadly, there actually isn’t a great way to regulate them.
Hat Placement
There are just a few other ways to place a pillbox hat. Personally, I are inclined to put on mine two methods. One look I really like is pushing the hat barely ahead so it rests about 1–2 inches above my eyebrows and tilting it only a contact to 1 aspect – Kate Middleton achieves this look completely. Alternatively, I’ll place my hat farther again and centered for a extra traditional really feel. For that, I take styling cues from Jackie O. There’s really no proper strategy to put on a pillbox hat, however these are the 2 placements I favor most.
Conserving Your Hat in Place
When you’ve determined the way you need to put on your hat, you’ll need to ensure it’s safe. If mine wants a bit extra stability, I’ll sew a small comb (or two) into the within lining. Then I frivolously backcomb a piece of hair, add a little bit of hairspray, and safe the comb into that space. Simple peasy.
The place to Discover the Excellent Pillbox Hat
Usually, I’d say pillbox hats may be fairly exhausting to search out, however since they’re at present trending, they’re extra available from a wide range of manufacturers and retailers proper now. When you can actually scoop up a brand new one from websites like Moda Operandi and Anthropologie, I’d argue that a few of the finest types are nonetheless present in local vintage and thrift stores, in addition to from artisans on Etsy.
My Present Favourite Pillbox Hats
With so many new types being launched, it was such a deal with to flick through totally different manufacturers and slim down my favorites. I’m at present loving all of the pillbox types from Lele Sadoughi and Gigi Burris. I’m particularly smitten with this leopard one, this pink option, and this perfectly classic style.
After all, you may’t go unsuitable with one thing that feels winter-ready, like this 1960s mink hat or this rich chocolate brown version. And in case you’re a bride-to-be, I am keen on this white pillbox hat and this gorgeous option with an exaggerated veil.
Spring & Summer season Types
Whereas most pillbox hats really feel inherently fall or winter as a result of their wool, cashmere, or fur fabrications, don’t overlook a spring or summer time possibility. This one is ideal at below $35, and I completely love this elevated woven version. Not solely are these types the proper accent for any warm-weather frock, however they’re additionally extremely simple to pack for journey.
The right way to Type Pillbox Hats
Okay, now onto the actually enjoyable half—learn how to fashion pillbox hats! Let’s dive into just a few methods I feel these items will look unimaginable in 2026.
A Leopard Look
Okay, first I’ve to take a stab at styling this fab leopard hat. For this one, I’d need to maintain the general vibe feeling retro and female. For an evening out in NYC, you would pair it with this red gown and drape a faux fur jacket over your shoulders. I’d completely end the look with a red lip and, for only a contact of drama, add this affordable brooch. If crimson isn’t your factor, no worries. Leopard pairs superbly with so many hues. You may’t go unsuitable with mild pink, emerald inexperienced, and even child blue alongside this hat.
A Marriage ceremony OOTD
Let’s play faux for a second and dream about being a bride. I might completely like to fashion this pillbox birdcage hat for a winter courthouse marriage ceremony. Pair it with this dress, which is the proper marriage (pun supposed) of a enjoyable frock and a tailor-made blazer second for the courtroom. To finish the look, you may’t go unsuitable with these crystal-embellished flats. They’re snug, beautiful, and will even function your “one thing blue.”
A Traditional Look
As a lover of classic fashion, I couldn’t skip styling a timeless black pillbox hat. I typically dream about this coat, and I feel it could look so elegant paired with one in every of these refined types. The fantastic thing about a coat like that is that it may be the outfit. I’d put on it with these satin olive pants and a classy, simple pair of black flats. This bag can be the proper of completion.
Resort-Prepared
Okay, utterly switching gears, let’s discuss resort wear. I’d like to fashion this woven pillbox hat, or this one, in a extra whimsical, warm-weather approach. Each would look excellent paired with this dress I not too long ago preordered and these raffia slides. For this outfit, I’d maintain the bag summery but elevated, like this drawstring style I’ve been eyeing. Discuss an ideal vacay look!
Closing Ideas on Pillbox Hats
It’s clear I’m very enthusiastic about this present pattern! I simply love how elegant, stylish, and timeless pillbox hats really feel – and all the enjoyable methods to fashion them. Will you be giving these hats a strive? If that’s the case, I hope these styling ideas and outfit concepts encourage you to experiment with them this season.
For extra style inspiration, remember to try 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
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