No, your eyes aren’t fooling you. The pillbox hat is on trend in 2025 and you have been seeing them everywhere — from Instagram to Pinterest boards. 

While the past few years have been hyperfocused on ‘90s and Y2K trends, this year has seen a longer press on the rewind button with the renaissance of retro aesthetics. 

We’re talking Jackie Kennedy inspo. And Audrey Hepburn. And Princess Di. But we’re also talking about Cynthia Erivo and Irina Shayk (for more recent sightings).

They’ve also taken over the runways. Among the brands that incorporated them into their looks include Valentino, Chloe, Loro Piana, The Row and Khaite.

The 411 on the pillbox hat

Now, you may be wondering why you need a pillbox hat in your wardrobe. We counter that with why not? It’s chicness in the form of a hat. It’s seemingly simple but also visually impactful. 

A pillbox hat is a brimless, small hat with upright sides.

And it’s not just one style — yes, plain is nice but there are also textured options as well as a myriad of colours. Think straw, velvet, and more.

There’s also a variety of ways to wear it. Yup, not just at the top of your head. Angled is good for distinct looks. 

It’s also so versatile, you can enjoy wearing it for different occasions. No matter if it’s a smart casual soiree or a high-fashion gala. And, yes, you can even wear one to your wedding!

The pillbox hats started becoming popular in the 1930s but reached its peak when Jackie O (nee Kennedy) started sporting the style in the ‘60s.

How to style a pillbox hat

Looking to incorporate the pillbox hat into your looks this year? There are tons of ways to style it. Here are some of our faves.

Casual meets classic

Don’t be scared to add a hat to your smart casual ensemble. Hair accessories and headwear instantly level up what would otherwise be a simple look. 

Here’s an idea: the classic jeans and white shirt combo. Add a vest for variety and top your look off with a pillbox hat.

For the best dressed guest

Heading to a wedding or another formal event? Pair your dress with a pillbox hat for a vintage-inspired look. Or better yet, wear one if you're getting married!

From work to wine

Who says you can’t dress up for work? Wear an outfit that can take you from the board room to the ballroom. You just need a hat for it!