Skip to Content

How To Wear A Pillbox Hat

How To Wear A Pillbox Hat
*This post may have affiliate links, which means I may receive commissions if you choose to purchase through links I provide (at no extra cost to you). As an Amazon Associate I earn from qualifying purchases. Please read my disclaimer for additional details..

Pillbox hats are the height of fashion. They are often worn by high-status individuals or celebrities, but they can be worn by anyone who likes them.

A lot of women love wearing these hats because they add an element of femininity to their outfits. There is nothing like adding a pillbox hat to an outfit that already oozes grace.

However, most of all, it is the style of hat that makes this type of accessory so attractive. It has a timeless appeal that cannot go out of style.

Women who want to create a fashionable statement need to have some knowledge about what to do when they choose a pillbox hat for themselves.

If you don’t know yet, then keep reading. We will provide you with useful information on how to wear a pillbox hat.

black and white photo of a woman wearing a pillbox hat

History Of The Pillbox Hat

The first time people wore pillboxes was in the 1920s and 1930s. In those times, many men were wearing fedoras.

These fedora hats did not look good on women, so women started to make pillbox hats. As more and more women began to wear these hats, they became popular. This trend continued until the 1950s. 

During the 1950s, women stopped wearing pillbox hats as much because they wanted to wear something different. Because of this, the shape and style of the pillbox hat changed.

The 1960s saw the introduction of the pillbox hat again. Many women loved the way old-fashioned hats looked, so they decided to start wearing pillbox hats again.

Nowadays, the pillbox hat is one of the most common types of headgear in the world. More than 50% of Americans own at least one pillbox hat.

What Makes A Pillbox Hat So Attractive?

There are two main reasons why people love pillbox hats:

  1. The shape and design of the hat.
  2. The fact that people used to wear them during earlier periods.

Pillbox hats are typically made out of velvet or wool. Occasionally, they may be made from real animal fur, too, but this is relatively uncommon.

One thing you should always take into consideration before buying any pillbox hat is its overall quality, as well as its construction.

Quality materials help improve the durability of your hat. You also need to ensure that it looks great when you put it on.

vintage pillbox hat

Picking Out A Pillbox Hat

When choosing a pillbox hat for yourself, think about the color of the hat. You can find hats in black, brown, red, white, blue, green, yellow, pink, etc.

You can mix colors too. For example, you can put a brown pillbox hat over a bright blouse. You can also wear a red pillbox hat with dark jeans.

When buying a pillbox hat, it is important to choose the right size. Do not buy a hat that is too small, otherwise you may feel uncomfortable while using it.

On the other hand, do not buy a hat that’s too big, either. Choose a size that looks good on your face and that fits comfortably. You can ask someone else to help you decide which size works best for you.

You can wear pillbox hats with any outfit. From suits to skirts, you can wear a pillbox hat with just about anything. You just need to match the right accessories with the right clothing.

lady wearing a black pillbox hat with a lace

Wearing A Pillbox Hat With Suits

Women who like wearing dresses often wear pillbox hats. They can be combined with any type of dress. However, there are some pieces of advice that you should follow when wearing a pillbox hat with suits.

First, you must try to avoid wearing too many layers. It is recommended to leave the jacket open, unless it is very cold out. Otherwise, you could end up sweating, and you won’t want that. 

Pillbox hats look amazing when paired with both similar colored items of clothing, and complete opposites. If you’re going out in public, you can wear a light gray suit with a pillbox hat.

Or you can wear a dark gray suit with a pillbox hat. Both will look great together.

If you want to switch things up, you can pair a dark gray suit with an orange pillbox hat. Or, you can wear a tan suit with a red pillbox hat. Honestly, anything paired with a pillbox hat will look great.

The combination of a black suit with a blue pillbox hat is something that looks absolutely stunning. This style goes well with almost every skin tone.

Some people like to wear a pillbox hat without any accessories. But others enjoy adding earrings, necklaces, scarves, and bracelets.

When pairing a pillbox hat with a suit, you should make sure that you don’t go overboard with your accessories. A simple necklace would be perfect.

And, as mentioned above, you shouldn’t add more than one accessory at once. Having two or three accessories adds emphasis to the hat, so you might want to limit yourself to one piece per outfit.

woman wearing a red dress and a green pillbox hat

Pairing A Pillbox Hat With Skirts

A skirt is a lovely way to wear a pillbox cap. If you are planning to wear a skirt, then you should take into account how much length you want to show.

The shorter the skirt, the more likely it is that you’ll see part of your leg. So, if you want to keep things classy, you can wear a short skirt.

Alternatively, you can wear a long skirt if you want to cover your legs. Just remember that longer skirts mean that you have to wear heels. However, no matter what length you choose, it’s always nice to wear high-heeled shoes.

A pillbox hat is a beautiful compliment to any skirt. You can wear a black skirt with a pillbox hat or a red skirt with a pillbox cap.

There is really nothing stopping you from wearing a pillbox hat and a pink skirt. In fact, this is probably one of my favorite combinations. 

lady wearing a pink pillbox hat

Pairing A Pillbox Hat With Pants

There are lots of ways to wear a pillbox with jeans. For example, you can wear a white shirt underneath a denim vest.

Another option is to combine a white button down shirt with a striped scarf. Then, you can finish off the ensemble by adding a pillbox hat.

If you’re looking for another option, wear a pair of jeans rolled up at the bottom. This isn’t exactly a classic option, but it’s definitely fun. Of course, you can also wear a pair of slacks with a pillbox hat if you prefer.

Wide leg pants look amazing with a pillbox hat. It’s the perfect mix of elegance and maturity. Throw in a flowy blouse, and you will look like royalty.

You could technically wear a pair of skinny jeans with a pillbox hat, but it isn’t a combination that will always work. If you do decide to try this out, try and pair a long, flowy coat or jacket with it all.

Also, avoid having too many patterns on your clothes. They won’t coordinate very well. You don’t want to look too busy, or else the whole thing will just be confusing to look at.

Pairing A Pillbox Hat With Dresses

For those who wish to wear a dress, there are plenty of options available. Pillbox hats can be worn in a variety of settings with dresses.

From formal wear to the more casual looks, you can rock a pillbox any day. As long as you can pick out the right color, a pillbox can will compliment anything. 

It gives you extra height to make you look taller, but not everyone might want that! Even if you don’t want the height, these hats just make amazing and mature accessories.

Plus, they come in a variety of colors, shapes, and styles. The best part is that you can easily change your hairstyle to complement the outfit.

floral pillbox hat on white background

How To Fit A Pillbox Hat

Making sure you get the right hat can be a difficult task. Your hairstyle and face shape play a huge role in determining how big your hat should be.

If you are going to wear a wig, you need to ensure that the band fits over your head perfectly. Otherwise, it may fall off during a ride or dance.

You should measure your head to find an appropriate sized hat to purchase. Once you’ve found the perfect fit, you can pick between colors and style them with your outfits.

Always make sure your hat is comfortable, since there’s nothing worse than wearing a hat that’s too small!

Start by taking the hat off and holding it against your own head. Be sure to match the measurements of the hat to your own head so that it’s comfortable. 

Once you have determined whether the hat will fit correctly, it’s time to take it to your local tailor if you want to make unique additions.

If you have the skills, you can even do this yourself! By taking it to a professional, however, they can ensure that only the best quality work is done on the hat. Once everything looks good from everyone’s perspective, it’s fine to start the fun!

Final Thoughts On Pillbox Hats

The pillbox hat is a great fashion statement that very few people are bold enough to pull off. From striking outfits to the more subdued and royal-esque, these hats have a place everywhere.

If you’re brave enough to try something new, this hat will pay off in the most unexpected ways. You can feel sassy or mature, and it’s all down to what you style with it!

Don’t forget to check our other articles and pictures for more inspiration! There are great ways to style and wear it, and only you can make the call that’s right for you.