How to Wear a Pillbox Hat?

Pillbox hats are one hat type that goes through different phases of popular and unique phases that make them easy to match your outfit style.

In the market today, you can get multiple sizes, colors, styles, and many types of genuine hats with a modern touch.

And one primary reason that you haven’t tried it is that you do not know how to wear a pillbox hat.

However, in this post, you are sorted because you will learn how to wear a pillbox hat and other helpful information.

What is a Pillbox Hat?

A pillbox hat is one of the smallest hats for women. The hat was first to emerge in the 30s, and it gained popularity through the 60s.

Due to the modernization of this hat nowadays, you can get this hat in various styles and colors.

As for its name, the pillbox was a small container designed to hold pills back then in the 1930s.

However, the haymaker bought the idea of the pillboxes and started designing styles of pillboxes for covering the head.

The original pillbox hat was small and had a level top, brimless and straight sides.

Once these hats were designed, they gained popularity due to their elegance and simplicity.

First, pillbox hats came in solid colors, but as the industry of pillbox hats continued to grow, different styles emerged.

Hence you could get pillbox hats with pins, jewels, net veils, and many other features.

What’s more, modern pillbox hats are made from different types of material and have more elaborate designs than others.

Some of the materials primarily used in making the pillboxes hats include wools, gold, beads, different types of fabric, furs, and many other ornaments.

Since pillbox hats are different styles available, this became a trendy fashion since they were versatile, and you could match it with your clothes or outfit.

Remember that these are the kind of hats that nowadays you can see the air hostess also using in the airplane.

Therefore, you can define pillbox hats as small hats that come with an upright side, flat and straight crown with no brim, and are named after the small cases used to hold pills.

How to Wear a Pillbox Hat with Different Outfits?

1. Floral Pillbox Hat with 1940’s-Style Blouses and Skirts – Spring or Summer Outfit

how to wear a pillbox hat with spring outfit

There are different collections of pillbox hats; however, with the floral pillbox hat, you will be able to get a stylish fashion that is best for the event of the season.

If you want to bang your summer or spring season with a stylish fashion that would match the season, this is an ideal option.

It is fantastic if you have a long hairstyle since you would drop your hair either on your side or tie and then fall on your back.

It will help you to give a compliment for what you are wearing on your head.

However, if you have short hair, what you can do is you can match the pillbox hats with other wearable accessories like bangles, necklaces, handbags, or any other of your choice.

2. Stewardess Oval Style Pillbox Hat with Dress – for Wedding Or Party

how to wear a pillbox hat in vintage style

If you are looking to look more elegant during special events like parties, cocktails, weddings, or other special events with an oval pillbox, then you can have a fantastic outfit.

This hat has the 50s or 60s perfect finishing with stewardess style. This hat goes well with a classic uniform or formal Outfit.

Note that when you select this hat, make sure that you go for the one that complements your skin color.

Then you can wear it with your classic dress or uniform. However, you can wear a matching dress with your hair color or the pillbox hat.

3. Vintage Pillbox Hat with Short Dress, Skirts, and Tights – Winter Outlook

how to wear a pillbox hat with winter outfit

It is another best outfit style that you can try.

With this style, you can choose a vintage pillbox hat of the color of your choice, but it should match the cloth you will wear.

With this style, you will have to wear an elegant dress or suit, and you will get a great outfit that is best for the winter.

Note that this outfit goes well with short hairs styles; if you have long hair, you will have to tie them on your back.

Also if you want and it best style for you. You can also curl or fringe them on the front since they also complement the look of this fashion.

Note that it is good to select the color of the cloth to wear or even the hat, then make sure you go for the flattering neutral colors, and you will look amazing in it.

4. Swirl Pillbox Hat with Swing Detail Outfit – On Business Days

how to wear a pillbox hat in business days

With the swirl pillbox, you will have to match it with a unique swirl detail outfit like your skirt or blouse.

Note that this is one of the styles that they will give you the classic style if you wear it with a skirt, blouse, handbag, matching shoes, and even glasses.

It is a unique one, and it’s a great style compared to the other pillbox hats. Since it gives you a couple of ways to do it with your hat.

Like how you are going to position your head either backside or tilting on your face.

Also, note that it is a favorite style for the long hairstyle.

5. Straight Pillbox Hat with Modern Outfit – Winter Stylish

how to wear a pillbox hat casually

It is a classic and vintage way that gives you a casual or modern outlook.

Note that this is one of the suitable styles for the short hairstyle since you will use the hat to wear your head straight.

It is the best option style or fashion special during the wintertime since you can match your winter outfit and mix it well with other outfits like jeans and many others.

If you want to try this option, wearing them with jeans, or skirts and a blouse can be a superb style you have ever tried.

6. Pillbox Hat with Veils and Elegant Feminine Outfit – Wedding and Parties

how to wear a pillbox hat on events

It is one of the pillbox hats you can use on special or casual events. For instance, if it is used with a veil, it can be a suitable choice for weddings during the wintertime.

This style is good since it adds a classic style to your outfit.

The hat can be added with other hair accessories, and it can give you a fascinating look.

Note that also this style is best suitable for both short and long hair.

Who Will Look Good With a Pillbox Hat?

The people who look good in pillbox hats are the women, and the age bracket can range from teenage to older women.

This hat was designed explicitly for women, and nowadays, it is one of the fashion trends among women.

Pillbox hats can be designed differently, and even in some cases, you would see women wearing them in special events like weddings and other thrilling events.

For instance, at a wedding, the bridal can wear a hat with unique features and styles like a net veil and many others.

Even though almost every woman can wear these hats, slim teenage and older women look more sexy and unique in these hats.

For instance, you can take an example of the air hostess, the way they look amazing why they are in these hats.

However, if you know how to wear a pillbox regardless of your size or age, you can look amazing.

How to Keep Your Pillbox Hat On Your Head?

There are different ways that you can use to make sure that you keep your pillbox hat on your head firmly; some of these ways include;


You can use the hat pin to hold the hat with your hair. Though it is one of the oldest methods, it is suitable, and it also adds some decoration to it.

Hat elastic

It is one of the other primary methods to hold the hat firm on your head. You can attach it to the side of your hat, and you will be able to go.

Bobby pins

With this method, you will need to have two pins, slide them to the side of the hat, and then push the hat back to your head.


In short, you have learned a lot about how to wear a pillbox, and now when it comes to the pillbox, you will not be nervous.

Note that wearing a pillbox is easy, and you don’t have to stress yourself out.

What you need to do most is go for the neutral colors so that you can match them with most of your outfits based on the season or the purpose of the Outfit.