securing a pillbox hat with bobby pins
Wearing hats

How to secure a pillbox hat?

Immerse yourself in the timeless allure of Jacqueline Kennedy’s elegant style as she effortlessly donned those iconic pillbox hats, perched gracefully at the back of her head. Have you ever wondered how these chic accessories manage to stay perfectly in place? Unlock the secrets to securing a pillbox hat with my expert tips and tricks and embrace this timeless fashion statement headpiece with confidence and grace.

Consider the size of the pillbox hat

Pillbox hats come in different sizes and shapes. In this blog post I will be discussing hats that are worn at the back of the head a la’ Jacqueline Kennedy style. For securing pillbox hats that are worn on the side of the head please read this blog post.

Jacqueline Kennedy style pillbox hats can be made as full size hats as well as medium size hats. The full size hats will cover most of your head and in some cases will not need any or very little securing. See the hats JOSEPHINE and INES as an example. The medium size hats are not as deep and will need extra means so that they stay in place. See the hats FILIPPA and RUTH.

Means for securing a pillbox hat

All of my hand made pillbox hat have a comb or a set of two combs at the front of the hat. All you have to do is lift up the combs with your fingers and then slide the combs into your hair (direction front to back). It is always advisable to first place the hat on in front of a mirror, find the best position (understand where the front brim of the hat should be) and only then secure it with combs. 

securing a pillbox hat with combs

I also sometimes add a mesh crinoline ribbon around the inside of the pillbox hats. You can thread bobby pins through this ribbon and secure the hat with bobby pins as well. You can add 1-2 bobby pins on either side of the head.

securing a pillbox hat with bobby pins
securing a pillbox hat with bobby pins

You can thread the bobby pins through the mesh ribbon before putting the hat on (see photo above). This way it will be easier to secure the hat. 

Keep in mind that it is tricky to secure a hat if your hair is freshly washed. If so, use some hair spray to provide a better grip. 

Hope you enjoyed reading my tips and tricks on how to secure a classic Jacqueline Kennedy style pillbox hat. Subscribe to my newsletter and never miss a new blog post about the beautiful world of hats.

You can find out more about securing headpieces also in these blog posts:

How to secure a fascinator?

How to secure a fascinator or cocktail hat?

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